My bf and I have been together for a little over a year. It was a strong connection from the start. He has always told me that my intelligence, drive, and independence were the things he finds most attractive. He balances out my high-strung with a more laid-back personality and he respects the fact that I am career-oriented (things that are very important to me).

Anyway, a few months ago we broke up over a weekend. Correction, he ended it because he wans't sure. We've had a few fights over the year and this freaked him out.  I really thought about things before we gave it another go.  Anyway, things have been good. Not perfect, but improving. I feel like we've been working on our issues.

Here's the problem: I saw his "pro/con" list of me.... you know, the list where you lay out the strengths and weaknesses of a relationship. The pros (and it was a long list) were not surprising, nor were the cons... Except he noted that I wasn't cool and I wasn't cute... The notes elaborated that I don't have a great sense of style, and he isn't excited about showing me off. Now I wonder whether I can get my confidence back in the context of this relationship….


Okay, I hear ya, that’s gotta sting. But S, a con list is always gonna slug you right in the gut. It’s all the tiny f-cking annoying things you do and say that grind on his nerves. The thing to keep in mind here is that the whole point of the exercise was to figure out if the good outweighed the bad, right? And seeing as you’re still together (YAY!) clearly, the good won him over. 

Sure, it doesn’t feel amazing that your man thinks that you’re a borderline geek with wack style, but I’ve got to assume that those “negative” qualities are some of the very same reasons why he loves you. Hear me out for a second because I'm pretty sure on the pro side he wrote down that he loves how self-assured, grounded and confident you are. Right? Do you see what I’m getting at here, S? Those basically null and void the nerd factor, and dude is obviously so enamored by all the other overwhelmingly wonderful things about you that in the scheme of things, your tack-ass get-ups aren't a deal breaker. 

I realize the tricky part is that you can’t "unsee" that list, but if you do want the relationship to succeed, you’re going to have to try and move on from this. Yes, your ego is a bit bruised, but the truth is that each and every one of us suck in our own special way. So what if your steez is a bit jacked? Go to Bergdorfs and buy a few outfits, or don’t. Your exterior is easy to modify, if that’s really what you’d want. Personality changes, well, they’re are a lot harder to change, so in my opinion I think this relationship still has a fighting chance.

Hope this helps and thanks for writing in! xx