Miss Information: How do I convince my friend-with-benefits to become my girlfriend?

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How do I convince my friend-with-benefits to become my girlfriend?

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Dear Miss Information,

I did the dumb thing and fell in love with my friend-with-benefits (but cut me some slack — friends are good, and the benefits were really good too). I want more, but she's not interested. Reason — and all internet and advice commentary everywhere ever — says to give up. But I can be patient and want to give love a little chance without actively disrespecting her refusal. So, if there were a one-in-a-million recipe for teasing the FWB into a LTR, what would it look like? She's brilliant, Miss Info — smart and funny and gorgeous and she understands me like no one ever has. How can I create the conditions for the possibility of a relationship but still respect her general wishes as my favorite friend? — She's Worth It

Dear She's Worth It,

If I had a one-in-a-million recipe for creating loving relationships out of reluctant partners, I wouldn't be drinking tea out of a measuring cup. (I'd be eating caviar out of a mug, because my butler did my dishes after he finished polishing all of my Nobel prizes. Thanks, Jeeves!) Since the creation of "love," "unrequited love" has been snarling and nipping at its heels. And it sucks so thoroughly that countless novels, epic poems, and pop-punk albums have been penned in the resulting tears. I wish I had better news, She's Worth It, but I think you need to move on.

A healthy relationship is a partnership of equals, a fifty-fifty kind of thing. This sentence is the biggest snag in your plan: "But I can be patient." Being "patient" might sound like the noble thing to do, but it's actually selling yourself very short. Instead of being an active participant in the relationship, you're demoting yourself to passivity. Then she's the one with all the agency: the power to stay or leave, break your heart or throw you a bone. Your ideal fifty-fifty is now closer to eighty-twenty. That's not fair to you, and it's not fair to her — you'd be putting a tremendous amount of pressure on her ("I love you! Don't fuck me over!"), while also putting yourself in a very weak and vulnerable position. You're stuck watching your phone, and she's stuck hurting you without realizing it.

I feel for you here, because it's a tough mixed message: "I like you within these parameters (sex, thrift shopping, brunch), but not those parameters (calling myself your girlfriend)." And herein lies the problem with FWB situations: they work only on the assumption that both partners can detach sex from emotion. Some people can do this better than others, but the arrangement requires both partners to be one-hundred-percent on the same page, which is a tall order. For what it's worth, SWI, your quandary is incredibly common, and you didn't do "a dumb thing." The inconvenient truth is that sex does engender feelings, and by acknowledging your emotions, you're being honest with yourself. That takes guts, and it's a step toward finding a happier situation.

There is a silver lining, though, SWI. I like your tone. You speak about this girl with a lot of warmth and respect, and your letter is commendably free from self-pity. It seems like you've got a good head on your shoulders; you know what's up, you just hope there's a loophole. The bad news is that I can't hand you a magic potion. (So much for my Nobel chances.) The good news is that you seem like a solid and kind dude, and there are legions of high-quality girls who would jump at a guy like that. I say shift your energy from "she's worth it," and start to realize how worth it you yourself are.

Dear Miss Information,

My girlfriend and I have been dating for ten months. I've been thinking about breaking up with her, but with the holidays coming up, I feel like I should hold off. To make matters worse, I've been invited to her family's home for Thanksgiving and Christmas. I don't see any way out of going to either of these: we are from the same area, and I will be with my family about eight miles away. But if I go down this road, I'm afraid it will just get harder. Where does it end? MLK Day? Presidents' Day? When can I gracefully bow out? — I Don't Want To See You On Groundhog Day

Dear Groundhog Day,

It'd be one thing if you stomped through her church's Living Nativity on Christmas Eve, announced "I don't love you anymore," flipped the manger and punched a goat. But it's early November, dude. She has plenty of buffer time for her tears to dry. The kindest thing you can do is be clear and decisive. If you aren't into the relationship anymore, treat it like removing a Band-Aid: quick, relatively painless, and with a little involuntary screaming. In practical terms, this means do it now. No Thanksgiving pie bake-offs with her cousins. No wassailing with her parents. No helping baste the turkey. Do it fast and keep her family out of it. That way, you'll be breaking up with one person rather than ten.