Sarah Weir
October 14, 2014 8:13 am

Dear Sarah,

I met an amazing guy my first year of college. After much hesitation on my part, I asked him out. At the time, he said he wanted to focus on school and didn’t want a girlfriend. That was 4 years ago. True to his word, he hasn’t had a relationship in all of that time. I know what you might be thinking—but he isn’t into guys.

We’ve slowly edged into the best friend territory, which is nice. But here’s the problem: I’m madly in love with him. I’ve been waiting patiently all this time for him to move our relationship to the next level. I’m terrified that he’s going show up with a girlfriend one day. In my heart, I feel like he’s the one, but my brain says to move on. What do I do?

—Patiently Waiting in Illinois

Dear Patiently Waiting,

The time has come to be bold: no more waiting for him, you need to make another move. You are probably stalling because it hurt when he turned you down initially, but what is there REALLY to lose? Imagine the absolute worst thing that can happen: he says “I love you as a friend, but I don’t really see us being in a relationship.” That’s it. That’s the worst thing (aside from some embarrassment, sure, but you can get over that). Life is way to short for you to be spending your early 20s wondering if he has boyfriend potential. If he rejects you, the world will not collapse in on itself, you will not need to be whisked away in an ambulance, life will continue as usual. OK, maybe a little more awkwardly than usual, but that will also pass.

So, you have two choices. My favorite technique: ambush him with a kiss and see what unfolds. Alternatively, if that idea makes you perspire and break out in hives, just have a heart-to-heart talk. He’s your best friend—he can take it and he’ll be kind no matter what. If you go the kiss-first-ask-questions-later route, good settings include: nature, your couch watching a teary movie, anywhere with a majestically romantic view. If it’s not meant to be, you really are better off knowing now so you can be free to meet other guys.

Be brave and let us know how it goes,

Love, Sarah

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