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).


To The Girls Who Wear Their Hearts On Their Sleeves


Samantha – I know you are tired of getting hurt. Trust me, I’ve been the shoulder to cry on enough times to know that wearing your heart on your sleeve puts it directly in harms way. However, from someone who has never been so bold, let me tell you that you are so much more impressive than those of us who just ‘keep it together’ all the time.

If it wasn’t already painfully obvious from my previous posts, I am not really the relationship type. Truth be told, I never really have been. I had one “serious” boyfriend for about a year (on and off for quite a bit longer) but that’s about it. I say “serious” because it was for him, but never really that big first love for me. Instead, I’ve had numerous one night stands, casual dates, and a couple flings, with the longest one lasting for MAYBE a month depending on your opinion of the timeline.

Honestly though, I have never been bothered by my singledom and truly love being a strong, independent women who don’t need no man *insert sassy snaps here*. The problem is that this strength is now my shield, and detaching from emotions has always seemed easier than admitting to wanting something more. In my mind, as long as I didn’t care no one could hurt me, and I played this mantra on repeat until I had everyone convinced (including me) that it was true. Yet, I have finally realized that it is ok to expect more from a guy than a late night booty call…during what is probably the most single-friendly stage of my entire life.

As a 22-year-old recent grad with no strings attached to anything, I am the perfect candidate for being single and having fun. Which according to this blog I have certainly taken advantage of the past few months.  However, after “throwing my cat” around, (pardon the ‘Easy A’ reference, in some ways Olive Penderghast is my spirit animal) I have decided to stop hooking up and start settling down, at least for a little while. This inconvenient epiphany is only further complicated by the fact that while I may want a relationship, it doesn’t seem like many guys do. I can’t find one eligible bachelor who wants to go on more than three dates, let alone make a go at an actual relationship.

So I began thinking that maybe it’s me. Maybe I’m too picky…Maybe I just don’t have what these guys are looking for. But, thanks to countless hotline blings and less than chivalrous requests for a lady of the night, I’ve decided that if that’s what guys want, fine. I am not what they’re looking for, and that’s ok too.

I have never been one who’s afraid to make the first move, ask someone out, or go for what I want…EXCEPT when I actually like the guy. It’s like the second I could make a real connection , I over-think, self-sabotage, and consequently shoot myself in the foot. And no, I do not think that this a unique problem, most girls I know would admit to overthinking every single ‘y’ in the often overused ‘heyyyyy’. The difference is that for someone who is generally so driven, I am a huge coward when it comes to a connection, and when one thing goes wrong I am quick to dismiss the guy with a casual “On to the next!” I can probably thank Tinder for this, as there is always a ‘next’ potentially waiting for me with an effortless swipe to the right.

From a strictly scientific perspective there generally two types of people:

  • Romantics: Believe that there is “true love”, if it’s right it will work itself out and that soulmates exist.
  • Work-it-outs: Believe relationships evolve and grow, and requires work from both parties to be right.

I always believed that I was a Work-it-out type as the idea of soulmates makes me roll my eyes more often than not. However, my quick dismissal of someone at the first sign of trouble definitely points toward a romantic ideal instead of someone willing to barrel down when the going gets tough. Perhaps I am more romantic than I thought and am just waiting for someone to crack through my hard exterior and expose an actual softie on the inside. Trouble is, I make it damn hard for anyone to break through – made obvious by my ex-boyfriend who said he felt like he didn’t know me after 5 years of friendship and almost a full year of what was supposedly my first love.

But, before this post takes a dark turn to depressing-ville (here I go, changing the subject when things get a little too raw) let me just say this:

To all the wear-your-hearts-on-your-sleevers, fly to NYC for a first date romantics, and true love believers, I applaud you. Sure, if you act like you don’t care you can’t get hurt. But the real inside scoop is that it is much better to have loved and lost, than been the person who hasn’t loved at all – and acts like they’re ok with it.

Let yourself be vulnerable, let your heart be excited by every new connection and don’t stop believing that your next first could be your last, because that takes guts. More guts than this girl ‘who always keeps it together’ has, that’s for certain.