Mr. Ego Boost


Samantha – This post is going to make me look like an asshole. I know it, I accept it, and am just going to own it because I promised myself to be honest on this blog. Ok, disclaimer over. Here is my date with Mr. Ego Boost.

It started on J-Swipe – because which of my stories don’t begin on a dating app these days – when I came across this guy that had gone to my elementary school. I know I know, why do I keep revisiting guys from my childhood? Not really sure, but it’s a good convo starter and he remembered me too, so we set up a time to meet for drinks after work.

On paper, we had the makings of a great date. Grabbed a beer, went on a walk and had sushi for dinner. He was very sweet and said all the right things, including claiming to be an incredibly honest guy. This turned out to be true almost to a fault, where he may have disclosed more to me than he probably should have.

For starters, I have never seen anyone so nervous for a first date. From the beginning of the night I knew I wouldn’t have to maneuver the awkward end-of-night kiss as it was clear from all the face-rubbing, lack of eye contact and visible forehead sweat that he wouldn’t be making the move.

Surprisingly no, this is not why I said this post would make me come off as an asshole.

Further, as a dating blogger and self-appointed subject matter expert, I have read quite a bit of literature pertaining to the world of online dating. One of the things included in almost every “How-to” post about first dates is to not talk about previous people you’ve dated. Though never having done this myself, I didn’t really understand why it was such a faux pas…I mean, what’s so bad about connecting over some of the undoubtedly horrible dates we’ve all had whilst navigating the modern dating pool? Well, let me share something the dating sites never properly articulated but are certainly right about:

You should NEVER talk about your past on a first date, because when you spend so much time talking about what you guys used to do and how badly your ex effed you up, it shows that you are probably not entirely over it.

Around this point was when we left datesville and Samantha the therapist stepped in. He kept harping on how ‘together’ I was in comparison to him, to the point where I felt obliged to stroke his ego and talk him up…to HIMSELF. This is not the best first date move either, because while I am by no means suggesting acting like someone you’re not, a little confidence is sexy! And telling your date that they can do better than you is probably putting the wrong idea in their head. Personally, I’m not looking to start off a relationship with someone who needs me to constantly validate their self-esteem and be reassured as to why I am with them. I have been down that road and found that you have to be happy with yourself before you can be happy with someone else.

See? Told you I’d sound like a jerk.

Now, I don’t want you to get the wrong impression.  I had a pretty good time hanging out with this guy that I had not seen for almost 15 years. When we got onto a topic he felt comfortable about, eye contact was made and we could actually joke around, making me wonder if I should go on a second date knowing it wouldn’t go further than that. At the same time, is it really fair of me to go out with someone again because I like hearing how awesome I am for two straight hours?

This is another indicator that I am a total asshole.

In a weird turn of events, his badly needed ego boost turned out to be a huge boost to mine. It was really nice spending time with someone so genuine and I would have loved for this one to have worked out. It’s really a shame that all the sweet things he did do, like giving our leftovers to a homeless guy and making me feel pretty damn special, were overshadowed by crippling self-doubt that turned me into his shrink instead of his date. I mean, he did pay for dinner and I did provide some solid advice, so maybe I should be looking into a career change…