Ask Isaac: I Am Julia Roberts in ‘My Best Friend’s Wedding’ — Help!

Hello, friend!

This is a situation I’m well acquainted with, because my fiancée Jenny was my girl-best-friend for four years before we got together romantically. In 2011, when I first moved to New York, we had a night out where the lines came close to being blurred, but she had a boyfriend and I was unceremoniously rejected, and it was embarrassing and awkward and uncomfortable for everybody concerned. I didn’t get the girl.

So I had to swallow my pride and my feelings, and make a decision: Get over it and be a friend, or feel resentful and walk away. I figured that the friendship was far more important than anything else (especially considering my faulty relationship history), so I stayed mad for a couple of days then got over it. We didn’t end up together until May of 2015.

If you’d asked Jenny back in 2011 if she saw a romantic future for us, she would have laughed, and it would have hurt my feelings. But if you’d asked me if I saw a romantic future for us in 2012 or 2013 or even 2014, I would have laughed along just as hard.

By swallowing my feelings and looking at the reality of the situation — she had a boyfriend, and it wasn’t going to happen then and there — what happened was that we developed a genuinely amazing friendship. We hung out a ton, we laughed nonstop, we were there for each other through trials and tribulations, and we were each other’s ultimate wingmen. The best bit: Unbeknownst to both of us at the time, we also laid an extremely solid foundation for a happy, romantic union down the line.

What I’m trying to say is that you need to look at the reality of the situation. He has a girlfriend. You interfering with that isn’t going to make anybody happy. You’re also away at college, so trying to get into a romantic relationship with somebody who has a girlfriend and who lives in another city is borderline preposterous. Even trying to have a conversation with him about any kind of potential romantic future is inappropriate, because he has a girlfriend, remember?

My advice is that you get over it. It’s hard, so this guide can help. Focus on yourself and where you’re at right now, and stop trying to cash checks that haven’t come in yet. When you see him, be his friend. If that’s too painful, stay away. But if you are able to be a genuine friend to him without any ulterior motives, you never know what might develop. At the very least, you’re going to get a lifelong platonic mate, and ain’t nothing wrong with that.

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Check out Isaac’s Instagram, Twitter and website; collage by Krista Anna Lewis; Isaac photographed by Melodie Jeng.


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