Q: So, for a little while now I have been seeing more than one guy at the same time. I like things about both (okay, all three), and I have no problem continuing things with them to a certain point… but I don’t know exactly when that point is, and I don’t want to do anything to be cruel or to harm any of them. When is it time for me to go for just one guy and break it off with the others?
A: You’re dating three dudes at the same time? I don’t know how you even do that. Where do you get the time? Where do you get the energy? Don’t you have a job or any interests other than, well, dating? How do you project-manage all of that? Your Google Calendar must be a f**king nightmare. I hope you’re better at the whole juggling thing than the woman I recently met who, almost immediately upon getting my phone number, sent me a text meant for another guy she was trying to go out with and followed it simply with “Well, this is awkward.”
Anyway, I acknowledge that this is a legitimate issue — especially these days, if you live in a city with more than ten people and have access to all those fancy apps and such. And it doesn’t have a concrete answer. It’s not just black and white. A lot depends on it, like how considerate of other people you consider yourself to be, how serious each person has been and seems to be, which one(s) you have had sex with and how good they were at it, and how good they are at talking, etc. The list is limitless. A friend of mine has been having this issue with two girls and it’s all I can do to give him any counsel without slapping him in the face and telling him to just be happy that he has on his hands the coolest problem there ever was. But to be honest, I’m glad I don’t have this issue. It’s a doozy. You can’t help but think that it’ll either blow up in your face and you’ll lose both guys, or you’ll make the wrong decision and spend the rest of your days wondering what would have happened if you would have gone with the blue pill instead of the red, as it were. That’s the bad thing about decisions: there’s always at least one choice you didn’t make, and often times (probably more often than not) it’s impossible, at least initially, to discern if you’ve made the “correct” one, the one that is best for you at the time and is best for you in the long run.
But at some point, you have to make the decision. One boy over the other(s). Unless you’re all into some sort of polygamy or woman sharing or Eiffel Towering (“Scandal” reference, y’all!) or whatever.
The litmus test I prefer to use in this scenario (and I have been in this situations before, thank you very much—though it was many pounds ago, back when I was willing to try harder, like f**king Avis) is I ask myself a question: would I be upset if I found out that one of the people I was seeing was dating other people, despite the fact that I, myself, am dating other people?
If the answer is yes (and you must be honest with yourself here) then you should break it off with everyone but that person. If you feel this way about more than one of these people, then you are in quite a pickle and you should probably not serial date anymore. Because you’re the kind of person who wants to date multiple people simultaneously, but you have difficulty handling it when they do the same.
Now, if you have been sexually intimate with one of the people who you are dating in an overlapping fashion, it’d be antiquated for me to tell you to not have sex with another person if you and the other dude haven’t had a monogamy talk. You probably want to test the sexual chemistry waters with people before entering a serious relationship (because you wouldn’t buy a car without test-driving it), but it can end up being bad news if you sleep with more than one dude in an overlapping fashion and allow this to go on for too long. Things get more complicated, and if the guys have the misguided perception that you are in fact in a monogamous relationship with each of them (explicitly-discussed or not), it’s a real dick move to get busy with all of them while you procrastinate on making a choice. (Unless everyone involved is agreed that things are kind of casual and you can go ahead and bone whomever you want, as long as you’re doing so safely.)
At the end of the day, there’s going to be one guy you think more about, whom you feel yourself becoming more emotionally invested in than the other(s). If you deign that the most thought about man is the one you would like to pursue for the right reasons (which is to say you’re not just more interested in one of the guys because he seems more aloof or hard to get and you’re into the chase), then you should break it off with the other guy(s). Then you should have the monogamy talk with the one you’re truly, truly into. Don’t do it backwards, because if you do, and the guy you’re most into doesn’t want to enter a relationship with you, you’re doing yourself no favors by settling for the one you felt less for. Never settle. Not even during cuffing season.
Good luck! I hope you don’t end up alone!