Dear Dana: I’m In Love With Two Men, How Do I Choose Between Them?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana:

I’ve been seeing This Incredible Guy for several months and am falling head over heels in love with him. He’s smart, funny, super hot, and great in the sack. He’s the total package and I can’t wait to see what comes next.

Sounds perfect, right? Well, here’s my problem: He’s not the only one I have feelings for.

A guy I dated a couple years ago has just resurfaced and thrown everything into a tizzy. We, too, were falling madly in love with each other, but he had to move away for work. Since neither of us were into the idea of a long distance relationship, we decided to let things fizzle. It was sad and painful and took me a while to get over, but I did…or so I thought. He recently reached out to me and said he was moving back to town and would love to catch up. So we met for coffee and all the old feelings came rushing back. I guess I was never really over him.

I know open relationships can work, but it’s just not for me. So I find myself at a fork in the road, unsure of which path to choose. Do I continue to explore what could happen with This Incredible Guy, or do I reopen things with The One Who Got Away? My heart aches for them both. I’m so torn. How do I choose? 




Dear Torn:

Do you really have this problem?

If so, you gotta give a girl a bit more information to go on. All I have here is a short, one-sentence description of each guy. So it’s “smart, funny, super hot, great in the sack” guy vs. “all the feelings rushing back” guy. Couldn’t you have thrown something else in there? A hair color or a hobby so I could say things like, “Well, if you don’t mind dark hairs in your sink, then he’s the guy for you!” Or, “a motorcycle is hot. Go with the motorcycle guy.”

Instead, what I have is a request to help you commodify and rank two human beings who are, you insist, basically the same. This Incredible Guy gives you hot present tense sex! The One Who Got Away probably gave you hot past tense sex! This Incredible Guy is funny! The One Who Got Away is likely also funny!

How can I help you decide between two vague humans of unknown hair color? I don’t know. The one who makes you smile? The one who cleans up after you cook him dinner? The one who gives you the best birthday presents? The one who knows your mom’s middle name? The one who has the best income? The one who has the best car? The one who is the best at the sex times? The one who holds you the tightest when you’re sad? The one who would never ask you to compete for his love with someone else?

You pick based on your picker, and your picker ain’t me. Your picker is your internal gauge that tells when something is yes, yes, yes right or when it’s no, time to go. But that gauge is either out-of-whack or was uninstalled, so instead here’s something else to think about: Does either guy know about the other? Are they aware that they’re in competition for your affections? Or are you keeping them unaware on purpose?

You appear to be comfortable in this situation. You’re torn, but also kind of stoked. Because what’s better than being love? Being in double love! All of the love! No matter what you do, no matter who you pick, you still get to be in love. Well played.

But this isn’t a choice between two fixed objects. This is a choice between two variable humans, who may not want to be in competition. Who may not want to be chosen.

Here’s a super important question: Does The One Who Got Away even know that he’s back in the running? You are equating This Incredible Guy, a guy who dates you and has sex with you and makes you happy right now, in real time, with The One Who Got Away who…had coffee with you last week. Do you see how those two things aren’t the same?

You want The One Who Got Away. That is your choice, but you’re afraid to make it because he dumped you once for a job and now that he’s back he’s only having coffee with you and being super chill about not proposing marriage or asking you to be his girlfriend again.

Catching up with an ex isn’t the same as rekindling your relationship. It may have just been coffee. In the past you fell for him, and then falling became crashing when he left. You mourned for your relationship, moved through the pain of the loss, but now he’s back and maybe, maybe all of that loneliness and fear that you weren’t enough to make him stay may have been worth it. Maybe that pain was a middle and not an end. Maybe you can tell your friends years from now, “And then he left and I was devastated, but when he came back I knew it had all been worth it.”

Does The One Who Got Away want you back? Ask him. But, before you do, cut This Incredibly Guy loose. He shouldn’t be your romance insurance, a nice body to fall back against if The One Who Got Away crushes you again.

If you don’t want to do that—if you want to insist that you love both men equally and you can’t bear to choose one over the other, then I implore you: Pick neither.

Because this isn’t high school and we don’t make people we love compete in a boyfriend derby. Dump them both and go sit in a coffee shop for the next six months and stare of out of the window and figure out why you’re such a glutton for love. Both of these men deserve to be in love with someone who wants them the most, over all others, without reservations. Walk away from one and then pick the other, or walk away from them both and go look at yourself.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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