Samantha meets Smith

Have you ever felt your heart squeeze? Not in a concerning way requiring emergency services or medical intervention…I’m talking about the oddly pleasant sensation that feels like someone reached into your chest and tightened their grip. You know that one? I call it Love.

Why do I describe this, you ask? Well loyal readers, I am in love. The jump in head first, all-consuming, giggle-for-no-reason kind of love. It’s true! When we left off I was a recovering toxic-relationship junkie, just on the other side of my most recent relapse with Mr. Man, and today I am a woman free from her vices. In fact, my last blog post declaring our finality was just a few weeks into my then-budding relationship, which is now almost 6 months long. How the hell did that happen?

Well, without belaboring the past or belittling my journey to get here, I want to try to summarize the last few months. Toward the end of August I was entirely trapped in an emotional tower of my own making. Given I am still in full-time work and full-time school mode, I didn’t think I could handle a real relationship, nor did I think I wanted one. Without a real need to leave Mr. Man behind, I didn’t feel like I had to, keeping me trapped in my tower for far too long. Now, I’m not one who typically subscribes to fairy tale tropes, but in true Disney fashion, it was my Prince Charming (Smith) who showed me how to break out from behind the wall I’d built around me.

Smith is unlike anyone I have ever dated. He is strong but kind, smart but sensitive and intense but doesn’t take himself too seriously. He is in a word, balanced, and I am in a word, not. My parents have always described me as going from 0-100 real quick, a pattern I have only reinforced through my experiences with men time and time again. But that’s why he’s different. He evens me out. I feel calmer around him without ever feeling dulled, something I have grown to truly cherish.

I feel like I almost didn’t have a choice but to fall in love with Smith. There was a time early on in our relationship when I did something stupid to try keep him at a distance, for fear of getting too close. As mentioned in the past, I’m one of those dumbasses who likes to push people away only to confirm their fears of being left alone. And can you really blame me? I spent a year holding back  emotions from the person I cared about, so being vulnerable and trusting of his feelings for me was way harder than I expected. Nonetheless, instead of letting me push him away with my typical habits, he (figuratively and literally) held on, showing me I could depend on him entirely. After meeting in undoubtedly the most stressful time in my life, he has loved me at every mood and brought me a sense of comfort that I’m very grateful for.

I am self-aware enough to recognize that I have a Type-A personality and fiend control. I (like most people) just want to eliminate some of the ambiguity that exists in everyday life. But this super busy schedule of mine doesn’t leave enough space to be a control freak and getting used to that definitely took some time…In my past, exes have complained that I never full let go and always need to do things for myself, a criticism I’d taken offense to…Why should they do something for me that I can do it for myself? I pride myself on being fiercely independent, but the extreme lengths I’ve pushed myself to this year have forced me to rely on Smith, not from a want but from sheer necessity. Part of me thinks that we might not be together if not for my busy-ness, which has forced me to relinquish my fear of showing weakness and to let my man bring me lunch when I forget it at home. He wants to help because he cares, and I shouldn’t misattribute his kindness as a sign of my own weakness, something I wouldn’t have recognized otherwise.

The past 6-months have been some of the best of my life. Though I’ve felt challenged like never before I’ve maintained a healthy dose of perspective as well. If work sucks or I get a shitty grade it doesn’t change the person I am or the fact that someone loves that person. To date, this blog has been used as to encapsulate the ups and downs of dating, with my friends (and I) finding it hard to blog about an ongoing relationship. Nonetheless, I’ll keep trying to keep up the blog, as my attempts to explain this healthy, promising and real situation has only reinforced how healthy, promising and real it really is. I don’t know what the future holds for us but I am lucky to have met such a wildly patient and understanding man and am excited to see what comes next. 

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So Tell me What you Want, What you Really, Really Want

Well Spice Girls – I wish it was that easy! What do I want? What do the boys that I’m dating want? These are the questions that have been roaming through my dating mind and to be honest I’m not sure if I have an answer to any of them, and lately I’m wondering if I really need to.  Where I’m at with my modern, mid twenties dating I’ve been wondering: how much do we really need to know what we’re looking for when we start dating someone?

Let me take you back to when I did know what I wanted. A boyfriend. That’s why I was on the apps, that’s why I was frantically swiping and that’s why I was agreeing to all of these first dates weekend after weekend. I just knew that one of these guys could be my boyfriend and that’s exactly what I really wanted. So off I went. Each date felt like a checklist. Cute, check, Job, check, Apartment downtown, check, (I’m shallow I know) and so on and so forth. After each date, there I went, thinking that I had just met the boy who was going to be my boyfriend, and live happily ever after with me *cue wedding bells. I was so certain after each date that I had found ~the one~ But clearly (still single) my intuition wasn’t totally accurate.

Here’s exactly where I started to get confused – after 2 or maybe 3 dates, things would fizzle. We’d stop messaging, they’d be “really busy with work” or they’d just tell me that we weren’t a good fit. Quickly, after each guy,  I could see it: yeah he was boring, the conversation didn’t really flow, we didn’t have much in common, maybe his suggestion of movie night at his place really did mean that he just wanted to hook up with me. All of these things had come into my mind during the date, but I was so quick to push them aside, because maybe it wasn’t really a big deal. Think of all their other great qualities, I would tell myself and smile through the awkwardness that was the date. What’s worse is thinking back, had things not fizzled out (often by them) I would have still been keen and wanted to date them. Why? They were nice, they checked my list and I could tolerate my time with them. Then it hit me. Because I was looking for a boyfriend, I would date anyone who wanted to date me. I didn’t think about our chemistry, or if I was even remotely into them, but rather I checked off a list – what would my family think, would they get along with my friends, would be photograph well together etc. (you can see how this went). I was so into finding a boyfriend, that I forgot to use the date to get to know them and see anything other than a boyfriend figure sitting across from me, who realistically could have been anyone.

Fast forward to me deciding I needed to regroup. Maybe knowing exactly what I was looking for was detrimental to my dating, and my chance at finding ~the one~. Maybe I needed to be more go with the flow, and take the time to get to know someone and just see where it goes. Leaving my Type A planner personality behind, I decided to step wayyy outside my comfort zone and try it. I went into dating again much more open minded. There I went on  dates, trying really hard to be much more selective and really focus on the PERSON in front of me, not just the idea. Now I felt more confident, because I was going on dates no longer to look for a boyfriend. After one long date of a guy who only talked about himself, or a boy with whom I ran away from so he couldn’t kiss me, I became much more selective in the people I would see, and it seemed to be working well.

Next, I met Mr. Hm. Mr. Hm and I hit it off on our first date. And I know I say that about practically every date I go on, but he wasn’t just “really nice and cute”, but it felt like we had more in common, and I even left the date with those butterflies fluttering in my stomach (something I’m cluing in is an indicative sign to someone being more than just a friend). After the 4 hour long date, I texted him thanks, we chatted and we went on with our weekends. I hadn’t heard from him but knew I wanted to see him again. So like a modern, strong woman I texted him first again, and waited for him to ask me out. I didn’t think much of it, because when we spoke he seemed interested so I rolled with it. We had continued to see each other, and go on all of the dates exploring basically all of the Christmas and winter fun we could find. I was so into him, but tried to balance it by being chill – I mean, I was no longer dating for a boyfriend.

My chill attitude steered me away from anything that would make me seem “unchill” even though these things bothered me. Our dates were great, and he was kind and respectful and our chemistry together was pretty good ;). However, our dates were often a week apart, and within that week I could go days without talking to him and he could go hours without answering me. Mr. Hm was so hot and cold, I was constantly wondering “does he like me, is he seeing other people, where’s his head at” and though I would ask variations of these questions to him – (though confirming we were exclusive) I never asked him to clarify anything about what he wanted, or where his head was really at. The entire time something about it seemed off, and I never had that same confident feeling of knowing where we stood that I had with other guys that I’ve dated. I wondered what it was – aside from the fact that he didn’t like dogs (which really should have been my biggest red flag to begin with) I couldn’t find the flaw that I was looking for. After two months, I felt constantly confused – when we were together things were great, but during the week I felt as if he wasn’t in my life at all. It was as if we kept taking one step forward, and two steps back. It honestly became exhausting.

After enough of my frustration, with some advice from a friend I messaged him what I wanted to ask, trying to figure out where his head was at. Two and a half months of exclusively seeing each other, I really only thought that there would be one logical response. Trying to convince myself I didn’t want to be a girlfriend and I didn’t care about the title, it became so clear to me that I did want that with him. And I wanted all of the emotional support and responsibility that came with it. I realized I was upset if he didn’t text me after a long day, or would wait to make plans with me – likely only after I initiated it.

After a weekend of talking post message, I was going to see Mr. Hm and was excited about it. At the end of our date where we chatted about real things: our families, our charity work our job prospects, he drove me to my car. As he pulled up to drop me off, what felt like out of nowhere he decided that we should end things. EXCUISE ME. I was shocked, I was confused and all of a sudden I was sad because in that moment I knew that I had wanted something more. Leaving me with a very fair, and a very respectful “It’s really not the right time for me” type schpiel that he wasn’t ready to be a boyfriend again, and he agreed that was very clearly where we were headed. Confused and sad, I said goodbye to Mr. Hm and questioned where things went wrong.

All of a sudden it dawned on me that I had wanted to date him the whole time, and was too scared to say anything. I tried to play it off overly chill, but in reality I did think about what it would be like to be his girlfriend, and I was convinced that it was just a matter of time. I overlooked his signs of being emotionally distant and never called him out on it because I didn’t want him to say something that I didn’t want to hear. All in this, I followed his lead and pretended I was okay with what he was giving me, all because I didn’t want to say I wanted him to be my boyfriend. His mixed signals paired with our complete coupley date-y activities left me longing for an answer I was too scared to ask for.

My overall conclusion is still TBD. I know what I want (I think), but how do I go about the beginning stages of dating not jumping to conclusions or just hoping a guy will make the decision for me.   When I wanted a boyfriend, I misread every situation but when I “didn’t want one” I misread everything too, leaving me to question how clear my intentions should be when I start dating. I may be naive, and think every guy really is just super nice – but how will I know which guy is right for me?! As I continue to try dating through the six, I struggle to find what that happy medium is, and how much it affects who I date and how long I date them. Hopefully one day I’ll figure out  what I want, what I really really want and how I can get it!

Stay tuned

To the girl(s) after me:

Carrie – Hey, it’s me. Someone you don’t know and someone you probably will never know.  The only reason why I’m aware we’re connected in this universe is because we were both intimate with someone who once meant a lot to me. I just have so many questions for you though and the unknown has been bothering me.

So you just started seeing him – my ex. I imagine you met on Tinder cause he never goes out or does anything social, including interact with humans.

Continue reading “To the girl(s) after me:”

Boston Babe’s Back!

FFS this post is delayed. Though unintended I have taken 2.5 months to get this sucker out…As such, here’s a little #TBT for your Thursday afternoon….

It was an ordinary November afternoon when I received a Snapchat message from good ole’ Boston Boy (upgraded to Boston Babe), my super sweet fling from the summer who took me to baseball games and held my hand at the dinner table. It said: “Hey, do you know any good places to eat in downtown Toronto?” I laughed to myself, realizing that this was exactly how he’d started our very first tinder convo (yes, I have that good a memory). I was in the middle of a drrrry spell…one that actually started when B-Boy left Toronto back in August. Work was out of control busy, I was studying for a grad school entrance exam, and had a general apathy toward dating of any kind, so ya, I didn’t hesitate setting up our date.

We agreed to meet at his hotel and I showed up nervous and excited. After all, I hadn’t seen the guy in almost 3 months and couldn’t even remember if I thought he was cute. He ended up getting stuck at work so I decided to make the best of the situation and grabbed a glass of wine and a seat at the bar. I ended up chatting to the guy at the stool next to me (don’t get the wrong idea, he was well over 50) and had a pretty hilarious time. I felt a little like the star of my own version of “Pretty Woman”, trying to set up a client while waiting for another to arrive. The gentleman asked if I was staying in the hotel, to which I replied: “Nope just visiting a friend” just as Boston Babe showed up, looking way cuter than I remembered I may add. I struggled to find my credit card and pay for the drink only looking up when the bartender yelled “THAT WAS THE SMOOTHEST THING I’VE EVER SEEN”. Always considerate, my Boston Babe had subtly paid the tab and grabbed my stuff. All I could do was muster a quiet “thank you” and grab his hand before heading straight for the elevators.

The rest of the night was honestly amazing. We hooked up, ate pizza in bed, hot-tubbed, hooked up, watched a movie, slept, and again hooked up. It was as if we picked up right where we let off and quickly transitioned from ‘what’ve you been up to’ pleasantries to meaningful conversation. I left the next morning, after enjoying a complimentary hotel breakfast, feeling elated and excited to see him again. Oh! and I mustn’t forget that the gentleman from the bar the night before turned up again, this time sitting across from me as I ate toast and scrambled eggs, while I kept my blushing cheeks pointed to my plate.

Fast forward a few weeks and I am in a full-on ‘fling-lationship’. I dub this term to explain the otherwise uncategorically expressed phenomenon: I was 100% in a relationship for a very defined period of time. We texted, ate meals together, talked about our days, and spent a lot of time together. By the last week of his trip I had definitely grown attached, more than to just having someone in my life but to him as well. We went skating one night and as he held my hands and skated backwards, guiding us around the rink I couldn’t help but think: “Why does he have to leeeeaaaveeee”. I was so happy to continue doing what we were doing that I couldn’t help but feel slighted to have found someone I get along with so well when he happens to live in another country. A country with a president like Trump no less.

We had some very deep life chats over the course of a couple weeks, even getting into our pasts and relationship deal breakers which is something I rarely share with my male companions. I admitted mine is overemotional guys…ya, I’m pretty callous…hence my hesitance to share. It turned out I needn’t worry, as his exes always complained that he didn’t open up and was too emotionally reserved…Well no wonder we friggen got along so well! I don’t like to talk about feelings with the guy I’m dating and he doesn’t like to talk about feelings. period.

Well, while our mutual fear of intimacy made for a perfect fling, it also made it kind of hard to understand if the feelings I was developing were real. By the end of his trip my mind had turned into a broken record  “Should I say how I feel? Could he feel the same way? Am I asking to be rejected by a guy who admittedly doesn’t open up??” I continued this one-woman game of ‘relationship chicken’, torn between taking a risk or letting this great guy just pass me by until it was suddenly our last night together and I still hadn’t said anything. You’d think I’d be capable of uttering a simple “Hey, I like you and I’d actually give this a shot…what do you think?”, but I just couldn’t bring myself to do it.

Despite my overwhelming cowardice we had a great night. Well, no…Let me clarify. I had a perfectly good night but he was clearly VERY off…to this day I don’t know what was wrong but he didn’t enjoy the physical part of our relationship in the same way he had throughout all the time we’d spent together prior. Maybe he was also playing relationship chicken and was more wrapped up in his thoughts than in my embrace? Maybe he had a rough day at work? Who knows. I

left the next morning knowing that it’d be the last time I saw him.  Whether or not he felt the way I did one thing was clear: neither of us had the balls to turn this into anything real and without someone stepping up to the plate we’d go down in history as the greatest potential relationship never to reach the major leagues.

We had a great time together and while losing him stung a bit, I was over it after a couple days and quickly dove back into work, studying and not giving a fuck about dating. I won’t be the type of girl always at someone else’s beck and call, so if he ever came back to T.O., single or not, our fling-lationship would remain safely where it belongs: on my blog.

How I Broke up with My Best Friend…Twice

I used to think that girls and guys could be just friends. I really did! I’ve had many guy friends in the past and am 100% comfortable bro-ing out. Hell, sometimes I NEED the testosterone in my life to balance out particularly dramatic periods of time. But I have finally accepted that in any very close male-female relationship, it is not possible to always be “just friends”. In fact, to quote my fave relationship guru and fellow DTT6 author Rachel Green, a guy and girl can only actually be friends if they both successfully pass the “Do I like this person” hurdle at least some point in the relationship. Why I bring this up you might ask? Well, for the second time in my life I have had my best and closest guy friend admit to having feelings for me and for the second time in my life I had to give up on a friendship that has been ruined by sex – or in these cases, a lack thereof.

Quick background on me: I lost my virginity to my best friend in Grade 12, told him I liked him only as a friend, lost that friendship, realized I liked him a year later, dated for a year, broke up in what can only be described as world war 3, and hooked up on and off for almost 2 years until that went down in flames. If our breakup was world war 3 then the finality of our relationship was world war Z, and the carnage was epic on both ends. I decimated that friendship and almost 5 years after our initial breakup the wound has not properly healed. Safe to say I’m pretty sensitive when it comes to the treacherous waters where emotion meets friendship.

Despite this, I got very close to one of my male co-workers when starting at my current job. We don’t have much in common in terms of interests but for some reason we just click. Over the last year and a half we have gotten incredibly close, spending time together outside of work constantly and ingratiating each other in our respective lives. He’s facetimed with my family, I’ve gone for dinner with him and his dad and as time went on the lines between us grew increasingly blurry. Nonetheless, it never seemed like a problem worth addressing..I didn’t think of him him that way and didn’t think about how he felt about me.

Cut to – August 2016 when this great friend of mine turned into a compete a-hole. Seemingly overnight my closest male ally had become my enemy, acting distant and insulting at every turn. He pushed me away and I just didn’t understand why.

Never one to shy away from conflict I confronted him, at work mind you, and asked WTF was up. Honestly, I thought he was going to tell me he had feelings for our DTT6 resident Miranda and was absolutely FLABBERGASTED when he instead admitted to having feelings for me. I was shocked, confused, and a tiny bit flattered. His feelings ran quite a bit deeper than a crush, and his hurtful behaviour stemmed from an inability to balance our friendship with how he felt.After a very uncomfortable convo where I had to straight up tell this great guy that I was not into him we left the office in separate directions, me understanding what I did to piss him off (answer: not love him back) and him needing some space from our friendship.

I am not so naive to think this never would have happened. Tons of my friends had previously asked what was up, either believing he was into me or otherwise gay, so I was really the only one surprised by this news.The only explanation that I can provide is it’s a likely combo of  denial and wishful thinking. I never would’ve wanted to hurt him or our friendship, so I pretended the notion of us as being an “us” didn’t exist for as long as I could.

But now everything was out in the open and I totally respected the need for distance. I  went about my days as typically as possible, patiently hoping things would rectify themselves. And like most things do, our relationship eventually did go back to normal. We talked more, hung out, and I just assumed that his feelings had passed. “Maybe he was confusing closeness with intimacy and never even really liked me like that” I told myself this and honestly, I believed it. After a little while I didn’t even think about that 2 hour conversation that left us both without a best friend. The facetimes returned, the dinners too and I thought we’d made it past the hurdle Rachel so eloquently mentioned at the beginning of this post. In fact, we got even CLOSER if that’s possible and spent every waking minute together, at work and outside as well. He became my “emotional boyfriend” and while I definitely saw the danger in that I ignored it. He made me feel happy, secure and cared for without having the pressure to define anything because we already had a definition: Friends. At this point I actually did think about what it’d be like to be with him in a more romantic way, and it just wasn’t there for me.

Then came the holidays, a hard time for all single people. After a very boozy holiday party we ended up back at my place with two other friends. While they chilled in the main room we went to my bedroom to roll a joint. We were standing by my dresser chopping the weed when he looked over and leaned in #StonerRelationshipGoals. Honestly, this couldn’t have been more perfectly choreographed if it was intended for television but as he leaned in I leaned out, narrowly missing his kiss.

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(I am soooo not proud of my next few moments but they happened so I may as well be honest). Though I rejected him pretty blatantly, I was very flirty the rest of the night, even telling him “You don’t need to regret it” when he said he didn’t feel badly about making a move because the moment felt right. Ya, I was being a huge tease and an even huge-r asshole, but I wasn’t really thinking and maybe enjoying the attention a little too much.

The next day I invited him to brunch with my roommate and acted like nothing happened. 3 days later I went to South Africa for a 2-week trip. We spoke often while I was away so I just assumed we’d had a weird moment but had gotten past it.  But when I went back to work nothing was the same. Fun and comfortable had been replaced by tense and forced and I was so confused. I didn’t even think about the almost-kiss as being the cause, the incident living deep in my long-term memory and clouded by 2 weeks of sun. Things became progressively more tense and I progressively more upset. How were we at this place again? I didn’t think he could possibly like me because he was always talking about other girls, or maybe this is just what I was telling myself.

We reached a boiling point at my roommate’s birthday, where even his best GUY friend admitted that the tension was palpable. I texted him the next morning saying things had felt off for a while and we couldn’t put off a conversation any longer. Apparently my timing was less than impeccable as he was heading to Florida for a week, so we promised to talk when he came back. A week goes by and he comes back to work on what turned out to be a horrible, HORRIBLE day for me. Separate from our issues, I had some pretty serious personal stuff going on, and he ended up passing me dashing out of the office mid-panic attack. Without me even explaining anything more than “I can’t deal right now, this is too much”, we went for a walk and he let me utter panicky nonsense on repeat for 20 minutes. Knowing we still had to talk he said he’d wait till things calmed down and made sure to check in days later to see how I was doing.

We finally had our talk. He told me that he isn’t over me and had been thinking about making a move long before the night he leaned in for the almost-kiss. I guess I hadn’t realized how far back our issues extended because I was away (or ignoring the signs). What really gets me is he admitted to intentionally waiting and acting cool while I was away because he wanted me to enjoy my trip…he was always putting me and my feelings first. Since I’ve been back it’s become too hard to be just friends and he doesn’t know if I can be in his life the way I want to be right now. Again, I totally understand, but this time it’s much harder. Maybe it was a result of all the other things I’m dealing with at the moment, maybe it’s because I wish we’d work out because who doesn’t want to fall in love with their best friend. I honestly don’t know.

What I do know is that all the weirdness fell away when he saw how upset I was at work and was still there for me in spite of how hard it was for him, and this realization broke my heart a little. He truly put me first, even before himself, and when I thanked him for his support I broke down into tears, something I’ve never done in front of him. You know what his response was? “You being real and vulnerable right now only makes me like you more”…needless to say if my heart wasn’t broken before, it was after that.

After this we sat around not saying much. Neither of us wanted to leave because we knew this was the last time we’d be just the two of us for a long while. It’s not fair to him to stay so close to me and it sucks for me to have to let him go, but what can I do? I let this happen by getting into a pseudo-relationship and now I need to deal with that. When he hugged me goodbye I felt him hold me in a way that was tragically final and way too reminiscent of an actual breakup, and it was painful.

So now we’re not friends.

We’re not in a relationship.

We’re taking space and I had to tell this guy not once, but twice, “I’m sorry, I don’t feel the same way” (But I kinda wish I did).

The Fling’s the Thing

I originally was writing this as a 2-part tale about one crazy week of my life. However, due to circumstances you can read about below, this story extends past one week. So if you need a refresher you can find Part 1 here.

Wow, you’re back! Ok… uhm, I really wasn’t expecting this!

JK I knew you’d be back. Reading my posts is like passing by a car accident: it’s a damn mess but you can’t bring yourself to look away.

Now, where were we? Oh yes. I had recently hooked up with King of the Douchelords and was feeling pretty low. So I did what every girl does when her self-esteem is reeling…I looked for validation elsewhere. Now don’t you worry my friends, I am acutely aware of how dangerous this can be, we’ve all been in the situation where you’ll settle for anyone just to get some attention. So instead of hitting up an ex or another potential fkboi, I turned to an option who seemed like the anti-douchelord: Boston Boy.

He had been messaging me consistently since our first date, making me feel pretty rotten for not giving him the time of day when he seemed like a great guy. I invited him over the following Sunday, this time to hang out in a park outside my building. It may sound dramatic but I was a little “traumatized” by the incident with King Douchlord two days prior (Part 1), and that combined with our very meh hookup was enough motivation to try keep him away from my bedroom. He didn’t seem to mind though and we spent all afternoon lying in the sun, chatting and sharing (more than) a couple of kisses. It was really sweet and exactly what I needed: time spent with a decent guy who I didn’t feel any sort of pressure to be with…he was heading back to Boston in 4 days after all.

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The following night, while home watching Bachelor in Paradise (#NoRagrets), he suggested coming over and I hesitantly agreed. I wasn’t down for another hookup that would leave me feeling anything but satisfied, but thankfully he did not disappoint. Our second hookup was significantly better than the first and it seems like he’d figured out how to use what (little) the good lord had given him. We hung out again the next night…I know, I know! 3 days in a row…take a chill pill amirite? He was leaving in two days anyway and we were having a lot of fun so it didn’t feel like normal rules applied.

I was glad I’d decided to give this fling a second chance, especially because this particular type works for me. When one person is local and the other is visiting it seems like the perfect opportunity for a successful fling as you can essentially do whatever you want without feeling like anything needs to be defined. The finish line is crystal clear from the get-go and for me and so many of my friends, the expectation of where something may lead is what mentally fucks with us the most. Between this guy and my love affair in Banff, I’m beginning to think I may be a spring fling queen.

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It’s actually really interesting if you think about it. I am the most successful with relationships when I don’t need to worry about the end game. Is this evidence that I self-sabotage by prematurely assessing how something will pan out or does it say something more general about modern dating? When we stop the bullshit, stop the games and just get to know the person we’re interested in, it’s pretty easy to build an awesome connection. Conversely, when you add all that “who texted who first” crapola, it ruins everything. I saw Boston Boy 3 days in a friggen row…and yes, that is a little excessive, but I can’t even imagine doing that if he wasn’t going to be disappearing at the end of it all. #FlingLyfe has shown me that being honest with someone and just acting on what feels natural is the best way to experience something that’s enjoyable and stress-free. Sure, that seems intuitive…but try it in practice I dare you! It is WAY harder to act easy and breezy when you’re planning baby names in the back of your mind during a third date.

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As usual I digress, and I’m sure you’re curious to hear how this whole thing played out. I was supposed to see him one more time before he left on Thursday and was happy to tie up my fling with a neat little bow. Well you know what they say about life right? It’s what happens when you’re busy making plans. His job got extended by a week giving us more opportunity to hang out and I saw him a number of times over the next week. Hell, my roommate’s boyfriend even met him.

Fast-forward to last night, I was set to see him once more as he left for Boston today, our 2-week fling-iversary #romancegoals. We met at his hotel and bar-hopped around the city sampling craft beers and apps for the next 5 hours. I’m not going to lie, after how awkwardly things had ended with my fling in Banff, I was nervous as to how my exit would go. Well, I’m happy to report that we have a fantastic night together and I left the hotel this morning with a kiss goodbye, my watch on my wrist (see Monsieur Formidable for reference) and zero awkwardness! He said he’d look me up if he was in town again and I was cool with that. I would also be cool if he didn’t look me up, but eh, that’s for Future Samantha to decide.

After discussing my night with Miranda this morning, she said she was surprised at how easily I could separate the emotional from the physical as I did spend a significant amount of time with this guy. I guess it must be because I was never really into him in that way. We got along great and feeling intimate with someone is generally nice, so it never felt like I had to separate my emotions, they just didn’t exist. I doubt that I would have continued hooking up with Boston Boy if he was local but that’s the beauty of this stage of life. We can make self-serving decisions, take risks and try things we wouldn’t otherwise all for the sake of having new experiences, both good and bad. All I can say is that the past 2 weeks have been a friggen whirlwind and that I’ve learned more about myself and relationships in 14 days than I have in the last couple of months. Baby steps people, baby steps.

King of the Douchelords

Disclaimer: I am writing this as a two-parter for those of you who frankly don’t care enough about my love life to subject yourself to this much reading. For those of you who do stay the course, I thank you and God help me. Part 2 here: The Fling’s the Thing

It all started about a week ago with a guy I’d been talking to on tinder. We agreed to meet up so he came over and we sat on my terrace drinking wine and chatting. When hunger struck we grabbed a bite, which he willingly paid for, before heading back to my place. We had a great connection, sharing a lot in common and I really enjoyed his company. It seemed only natural that he’d stay the night, which he did, but the next morning I couldn’t help feeling underwhelmed, in all departments if you catch my drift.

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As a consultant in town from Boston, he seemed like the perfect candidate for a fun little fling, but if I wasn’t interested in what this fling could offer then what was the point? Despite the okay hookup we kept chatting on and off but I wasn’t sure if I would see him again.

Fast forward to Friday night while out with some people from work. We were having a great time and I was vibing with this guy who I’d always thought was cute. He’d had a girlfriend till about a week prior but was now single so….I’m sure you can see where this is going.

Well, however you think this story ends, you’re probably wrong.

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Cut to the next morning after he’d gone home. I recounted the details of the night to Miranda who’d been out with us only to realize they were pretty friggen horrendous. I remembered feeling insulted and uncomfortable a number of times the night before but became increasingly bothered as I spoke the deets out loud… A highlight reel of my night with king of the douchelords:

  • We hook up and I immediately get a speech all about how I need to be aware that this was just a hook up, he’d just gotten out of a long term relationship and how I wasn’t to try trap him in something. Uhm excuse me sir? Could you be more patronizing??? You cleeearly know nothing about me because if you did you’d understand that I don’t want anything from you either. But ok, whatever, guys give this speech all the time (as I would soon find out) so I let it slide.
  • We continue to hook up and I kiss him – as normal people do – only to be asked why I had done that when we had just clarified that our hookup was strictly physical. This is when I started to say WTF. I am not a prostitute and will absolutely kiss you if you’re in my bed, its part of the package deal. I can separate kissing from emotions and if you can’t then that’s your problem, not mine…Douche.
  • And finally, the piece de resistance: he actually tried snapchatting a post-coital pic of me to his friends! And his response to my protests? “Don’t worry; your boobs don’t have to be in it”. WOW, really? Thanks so much, you’re such a great guy!!!

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If you can believe it he still had the audacity after all that to tell me that we should keep this between the two of us. Yea, cuz snapchat is a very private and intimate realm…Sorry bud, no can do, this is 100% going on my blog.

I couldn’t believe the rudeness of his behaviour, but you must remember that I was drunk too and ended up making a (BIG) mistake. He slept over – I did ask why the F he’d wanted to given his many rules about what “just a hook up” means – and we ended up hooking up again at 6:30 in the morning. He immediately ducked out to get ready for a noon brunch and….I know, I KNOW! Not only does that reasoning REEK of bullshit but I definitely shouldn’t have hooked up with him again. Uch, I never claimed to be innocent in this story.

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Anyway, those are the main points I’m actually willing to share about this experience but let it be known that this isn’t an exhaustive list of his douchebaggey behaviour. Obviously, I was really upset about it the next day, at him but even more so at myself for not having more self-respect. I was used but I had let myself be used and that was a tough pill to swallow.

I ended up moping around for the entire next day, feeling cheap and pretty disappointed in myself until sometime in the afternoon Charlotte mentioned she’d come to a male-related epiphany over a laffa wrap. Well, I couldn’t find any decent middle-eastern food, but I did find some peace after a long walk and a seriously emo playlist, and decided I would just chalk it up to a shitty experience that didn’t have to define me.

I’ll pause here, so if you’re only interested in hearing about one of the worst hook ups of my life then feel free to stop reading. But if you’ve been paying attention and are wondering what happened to Boston Boy I suggest reading on, because my next post is when I stop being a hoe and start getting real. The Real World – Toronto Edition.

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Mr. F*** Boy

Guest Post!!! The following entry is from our newest contributor to DTT6 and we know you’re going to love her 🙂 Sign off in the comment section below and let us know what you think. 

I am excited to share with you quite an exhilarating story that is quite out of character for me. The experience taught me a lot about myself, what I want in a man and more importantly all about the modern day fuck boy.  We have all heard of him or encountered him  – the boy/man who at the end of the day just wants to fuck and nothing else. It can be quite fun but does the short-term pleasure make the potential long-term aggravation worth it? Lets find out.

We matched on JSwipe and our conversation quickly escalated to the topic of “What brings you to this app?” He blatantly mentioned that he was strictly looking for someone to connect with on a physical level. At first I was a little weary but after casually talking for a few days his texts made me straight up horny. He expressed everything he liked in bed and explained to me that he definitely had a kinky side. He sounded spontaneous, exciting and made me feel comfortable about my desires and fantasies.  We would text all day until finally I couldn’t take it any longer – I wanted this guy! I wanted to unleash my wild side and told myself to have fun and go for it so we planned to meet up.

At approximately 9:00pm on a Thursday night, after a fashion show, I stood at the corner of King and John waiting for Mr. Fuck Boy to roll up and pick me up at the side of the road. (Seriously how fucked up and unsafe is that.) I entered this stranger’s car with a lot of nerves but they quickly faded away after he greeted me with a kiss! I was totally taken back but after we started to talk I couldn’t believe what a normal and nice guy he was. He drove to Cherry Beach and parked his car in the parking lot upon arrival. We wasted no time and had sex in the back of his car. Due to the lack of space, limbs were everywhere, clothes were stuck and we were very squished and close together. Positions were limited but this romp got the job done. I was satisfied. The chemistry was great and overall it was a totally fun, carefree and awesome experience. He drove me to where my car was parked and that was it for the night.

We made plans to do it all over again a few days later at a hotel that he had booked. To be honest I felt like a hoe meeting a guy at a hotel but YOLO. The sex was much better in a bed this time around and I found him to be quite cuddly for a Fuck Boy. After getting to know him more and having him tell me that he was not interested in engaging in any activity other then sex, I realized that I was just another casual fuck girl of his.  This guy was totally all about “why buy the cow when I can get the milk for free.” It didn’t sit very well. I didn’t want to be cuddled and caressed by someone I couldn’t catch feelings for. Overall, I had a great time with him and really enjoyed myself. We parted ways a few hours later with a quick kiss and left things as “see ya later.” He went three days without texting me, which is not necessarily a bad thing, but after I responded back to that message it took him another three days to respond. Ummm what? Mr. Fuck Boy better had his thumbs cut off or something?! Too long. Point blank, unacceptable in my opinion. Three days for a response did not sit well with me, like come on you’re not dead. After addressing this behaviour as a major red flag I realized that even if this was just a casual romp I should be texted back within a decent amount of time and at the end of the day I want more than just sex. I want a great dinner companion for the pre or post event – like lets be real! Anyways, after he expressed interest to meet again (after mentioning that he has been really busy lately) I politely declined telling him that even though I really enjoyed sleeping with him and that I had a truly amazing time, we wanted different things and it was best to not do it again. He put up no fight and accepted what I said with an “okay.” The End.

I learned a couple things about myself. Firstly, I definitely have a kinky side that I’d like to further explore and secondly I’m a total sex goddess and proud of it.  Despite these lessons, I realized that as a classy woman with high self-esteem, it is important for me to be treated like one. I know that I am more than just a body for some guy to fuck and its okay to say no and not give in especially if it won’t make me feel good or give me what I want.  There have been moments where after spending time with other boring guys who don’t sexually excite me I have considered re-connecting with Mr. Fuck Boy but at the end of the day I remind myself that it is just not a good idea. My advice to all you classy bitches out there is to know your self worth and don’t settle for a Mr. Fuck Boy who can’t give everything you want.

The Click

101009784Everyone has had a similar experience, whether with a friend or a romantic partner, you’ve met someone and instantly “clicked”. From the moment you two saw each other there was some sort of a metaphysical connection that drew you to one another.

It’s something more than mere attraction, it is as if something in the universe says you two need to connect. There’s no fighting it, like two magnets pulled together, your attraction is guaranteed.

I met K last summer while staying at a hostel. A friend of mine had a little too much to drink so I ended up dragging her butt back from the bar and taking care of her for a solid portion of the night. While sitting on the floor holding a garbage can to her face and trying to force feed her bread this insanely handsome guy came down the stairs and took a seat on the steps right in front of us. He kept me company while I consoled her and stayed to keep chatting after I finally managed to put her to bed.

We only spoke for a few hours that night because he had to catch a flight home in the morning. With no kiss or steamy one-night stand, we added each other on facebook and parted ways.

I’ve never had such an immediate connection to another human being. In those few hours I felt as though I wanted to tell him everything. It was an indescribably feeling, as if we were meant to play some sort of role in the others life.

After our wonderful chat I came to terms that I would never see K again but just a few days later he contacted me. We ended up speaking almost every day for a year. He became one of my closest friend. On the rare occasion, when we would video chat rather than message, we would talk for hours about everything you could image … our friends, travels, politics, aspirations and most importantly, one day, seeing each other again.

A year later I get to finally see my newly found best friend in the flesh. Against all odds our connection has maintained it’s strength and will soon be bringing us back together.

I have no idea if this person is meant to play a larger role in my life or not. Perhaps as a friend, companion, lover, or maybe our journey is intended to end upon our reunion. I can’t anticipate what will happen, but I’m excited to find out.

Mr. Somebody That I Used To Know

Carrie – Okay Mr. Somebody might not be the story you’re expecting. It definitely wasn’t what I was expecting when I boarded the subway at Finch Station on a Thursday morning at the crack of dawn. I had been staying uptown at my parents’ house, the area where I had done (most of) my growing up. Disoriented from taking the southbound train to work, I got in on one of the cars in the middle. And out of all the ways I changed my normal routine that morning; it was either fate or chance that led me to stand in the same car right across from Mr. Somebody.

So who is Mr. Somebody That I Used To Know? Well, he is the older brother of my ex, aka the only boyfriend I’ve ever had, aka Mr. High-School-Sweetheart Puppy Love. Mr. Somebody was the quiet eldest brother of three, equally as mild-mannered as my ex, but definitely the most difficult to get a reaction out of compared to the rest of the family. Going from playing board games with him once a week to deleting him off Facebook when I found out my ex was sleeping with someone else, it surely was an odd feeling to see him again and I wasn’t sure how the interaction was gonna go.

Continue reading “Mr. Somebody That I Used To Know”