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These questions continue to amaze me. As always, Anonymous’ question is in quotes below.
Cue 2004 Usher: these are my confessions.
I’ve read all your columns and I’m hoping you’ll be able to help me out here. I’ve recently moved to a neighborhood in Cincinnati where my ex from college is also currently living. We dated for 2.5 years before an explosive breakup senior year, but continued to find ourselves in each others beds multiple weekends throughout the year before graduation.
Anyways, I had let her know via snapchat that I moved to Cincy, and five days later I found myself in her condo, naked, for the majority of the 9 hours I was there. We have continued to see each other, go to dinner, drink wine, and have sex almost bi-weekly since I moved here. We spend full days together ignoring the outside world, and then go back to our separate lives as soon as I leave. I know she’s sleeping with other people, and I am too. We do not discuss ever getting back together but I know deep down that I want to. I am seeing another girl Katie, sort of on the side, but the entire time I’m with her I feel guilty because of Jenny. Katie is a total babe, all my friends love her, and I kind of want to move things along, but lingering in the forefront of my mind is ALWAYS FUCKING JENNY.
I’ve drunkenly brought up getting back together to her only to be told that it’s “not the right time in her life” and she needs to “find herself” before she can even consider getting back together with me. I’m 25 years old, feel like I need to settle down, and can’t choose a girl. Do I wait for Jenny’s dumbass to come around and finally be with me, or attempt to move on and get things rolling once and for all with Katie? Or, just continue to fuck them both and wait around for father time to take care of things? I’m afraid if I end things with Jenny and go all in with Katie I’m going to regret leaving her.
My friends are no help and continuously call me a “hollaback boy” because I keep returning to my ex. Fuck that nickname. HELP ME JOHNNY D.
Jesus, man. This is quite the dilemma. And Katie sounds like a catch. But you wouldn’t have sent this question to me unless you were still on the ropes about your ex. And that, my friend, is one of the worst places to be. I’ve been in your shoes before. And I hate to tell you this but it’s not looking good on my end for your girl Jenny.
You like having sex with Jenny because it’s familiar. Look, ex-girlfriend sex is awesome. You guys know each other’s preferences in bed already. You know what she likes, she knows what you like. It’s easy. There isn’t any awkwardness between you (unless you’re talking about getting back together). But you guys broke up for a reason. You conveyed that it was messy, too, which leads me to naively assume that the two of you were fighting a lot. I think you need to take a step back for a minute and weigh your options. An honest evaluation without rose colored glasses on about the two-and-a-half years that the two of you were exclusive. Ask yourself why you guys broke up. Was it something you did or was it her? Did your friends like Jenny? Was there infidelity? Do you like Jenny as a person or do you just like having sex with her? Can you handle the backlash that’s probably going to come your way if you get back together with her? These are all questions that you need to factor in. Waiting around for someone to have feelings for you is not a good idea. And hooking up with an ex ends in one of two ways, almost everytime.
So here’s what I’ll say. I say you sit Jenny down and ask her straight up if she wants to get back together. My prediction? She’s going to get pissed off and tell you she doesn’t want to hook up with you anymore. Right now you’re toeing a very ambiguous line. If you tell her you want to be exclusive she’s probably going to get nervous that you’ve caught feelings and cut off the arrangement you have. If she says “yes, let’s be exclusive” than you’re now in a spot where you need to cut things off with Katie. If it were me? I’d bail. If she’s still singing this tune about “finding herself” (which is so disgustingly cliché I can barely stand typing it) I’d say it’s time to hang up the cleats. Leave her in the dust.
It feels like you’re still pretty hung up on Jenny and she’s not all that into you. Fuck that. You’re not a chump. If she is still giving you these bullshit excuses in a sober setting just get out of that situation. Roll the dice with Katie. She’s new and you said your friends love her. That’s pretty tough to beat. But what the fuck do I know? I’m a jackass. Up to you. .
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