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Should I do more kissing with my hot friend?

Love Letters
Love Letters

Q. I guess I’m wondering what you do when you’re walking the fine line between friendship and something more. I have this great guy friend who I’ve been close to for a few years now. He’s seen me go through boyfriends and helped me get through some hard times. He had a girlfriend when we met, but I never met her because they broke up soon after.

He likes to take things very slow, which is fine, but then he has a tendency to randomly flip a switch on girls he’s dating and only wants to be friends again. I’ve noticed a pattern.


Another thing is that sometimes he will start talking to a girl again, flipping that same switch. Before the commenters rip him/me apart, he isn’t sleeping around. He makes it pretty clear to these women that he wants to wait until marriage (and I know he is straight).

Anyway, over the last few months, the tone of our conversations has shifted a little, and he started throwing out really sweet compliments about me. I returned his energy because he’s definitely an attractive guy, and it was interesting, I guess. Then, we were watching a movie at my place recently, and we shared a drunken kiss. We never really talked about it because it was just one kiss, but he did say I wasn’t a bad kisser on the phone a few days later.

I’m not stupid and I don’t want to jeopardize a friendship I value a lot by changing the dynamic. I also don’t want to be another girl he drops suddenly, but the guy managed to get in my head and now I’m thinking about him. I really do love this guy (in a best-friendship way) and I’d be lying if I said that over the years I didn’t think about him as more a few times. I don’t know if I should pursue a potential relationship or if I should keep the friendship. There’s definitely a million movies that say we’ll start dating, fight, and then kiss on a doorstep with happily ever after as the screen pans out over New York, but any other advice, Mere?



A. They never show you the scene that comes after the screen fades to black in those movies. I imagine that’s because some of those friends-to-enemies-to-lovers relationships burn out in the long run.

But ... do you even want a happily ever after right now?

You know this man flips a switch on women. He’s in it ... until he isn’t. It doesn’t seem like he’s looking for the person he’s going to marry. But you might not be either. I don’t get the sense you’re ready for a forever kind of commitment. In fact, the only thing you’ve made clear is that you like the friendship and think this person is hot. Maybe you’d be OK with some ambiguity and more kissing.

Think about how you’d feel about something casual. I’m not a huge supporter of friends-with-benefits relationships because ... well, the letters about them sound kind of painful. But I imagine there are a zillion people who make them work and never write to advice columns because they’re having so much fun. Also, can you continue to look at other people while considering him? Is it all or nothing?


My last thought is that the line has been crossed; he’s already more than a friend. At the very least, the two of you should talk about what’s changed and what you’re willing to try. You also want to make sure you have a few platonic friends in your circle. I’m not sure this person was ever 100 percent friend, but he’s not your person for stability right now. That’s OK, by the way. Relationships change.

I guess I’m giving you a big “maybe.” Think about what you want, what you’re willing to try. Ask him if he’s thinking about it too. If you can drop the happily ever afters and focus on today, there might be something there.



The thing is, eventually you will lose this guy’s friendship if it doesn’t become something more. The fade-to-black will be him going off with some other girl and his focus staying on her after they marry and you never hear from him again. Might as well take your shot at being that girl, letter writer.


How does just one drunken kiss happen with no dialogue afterward? You both kiss, but no one tries anything more so you just turn back to the TV and say nothing? That in itself is quite odd. At least one of you should’ve taken it further, attempted to show interest. It seems really awkward. I’m not on board with waiting until marriage either. This guy seems lukewarm at best about having hot and heavy ANYTHING. Proceed with caution.



I wouldn’t get overly excited about one drunken kiss, especially when his reaction a few days later was only to say that you weren’t a bad kisser, not something more romantic or telling you that his feelings had changed. If you want to give it a shot, you can ask him if he can see you as more than a friend. You should have a good idea if he’s looking for a relationship or not if you’re really close friends. If he’s not, it’s probably a waste of time and you will end up not being friends.


The solution is to communicate with him. You don’t have to “chase” him. Just ask him: “So, what was that kiss about? Are you into me as more than a friend? What about the way you treat girls you’re dating?” See? It’s easy. Just make him talk about it. And you have to talk about it too. In person.


Send your own relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.