Should I Ask if we’re More than Friends?

Dear Em and Lil,

I am a straight woman and am friends with a man. We have been close for years and years and have sporadically dipped in and out of romantic interest. About once a year every year we flirt and maybe become romantic, and then we continue as friends, never discussing. I am not sure if I need to be romantic with this person, but the tension and romantic frustration makes me feel like a teen again, and not in a good way. How do I ask if we are more than friends or, perhaps even better, not be obsessed with this question?

Sincerely,

Will we Won’t we

LIL: The best way to get past that teenager feeling is to start a conversation with your friend. You don’t need to make it the most profound talk ever, or even ask right away if they think you’re more than friends. Start by just acknowledging what has been going on, and that will demystify things and make it easier to get to the bigger questions whenever the two of you are comfortable. It might help to call out the weirdness of the situation by saying something like, “so, we’re just never going to talk about our little annual tradition, right?” Your friend is probably feeling confused and slightly obsessive just like you (he hasn’t yet written to us, so I’m guessing he went to our rival column, Ask Lem and Mil.) It will be a relief to them if you bring it up. 

If you do want to keep this thing going, talking to your friend could open the door for romance to happen again, or more frequently. But it sounds like you’re not sure you’re interested in that. What the two of you are to each other will be up to you just as much as your friend. You should try to think about what you want. It might help to imagine possible future scenarios, and how you would feel and react. For example:

  • Your friend tells you he has romantic feelings for you.

  • Your friend starts a (monogamous) relationship with someone else.

  • Your friend tells you he wants to keep things exactly the same as they are now.

  • You go to the airport to catch your flight (to Paris for your dream job at a fashion magazine!) Your friend finds out and goes after you, catches up just in time, and tells you that he loves you and he always has just as you're about to board the plane.

People say, “I don’t want to ruin the friendship,” when they’re in this type of grey area. But I don’t think it’s usually romantic tension in itself that causes friendships to break down. What does it is the feeling that you can’t be yourself, or that there are suddenly all these taboo topics, and you need to keep your company manners on around someone you used to be comfortable with. Be honest with your friend and ask for the same from him, and you can get to a good, post-teenage place, whether you end up being just friends or not.

EM: The more than friendship dance… so tantalizing, and so frustrating. Will they get together or won’t they? Letter writer, I don’t think you should get together with your friend. In fact, even you don’t think you should get together with your friend (readers, consult question line three for evidence). Since you have known each other for years, you both have had ample time to decide if you want to take things further. For whatever reason, (timing, interest level) one or both of you have relegated this relationship to the in-between place: not quite there, but not quite not there. 

Some people are happy to remain in the in-between place. This situationship may work for folks who want something that is low commitment. But since you wrote in to us, I suspect this romance-friendship isn’t giving you what you need.

I think people usually get caught up because they prioritize getting the person they want over getting the relationship they want. For instance, I may want to have a fling with Michael Cera and end up compromising for an enduring and beautiful marriage because of his preference to settle down (dammit, Michael). 

Step one is to figure out what type of relationship you need and step two is to find someone who fits the bill. Do not smush a non-committal guy into a relationship; you will only waste your own time. Sure, it’ll take longer to find a person you like who also fits into your life. But, trust me, as a gal who has tried to convince someone to be my boyfriend who didn’t want to, it is infinitely better to wait for someone who is on the same page.

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