Monday, March 7, 2011

Dating Three People at Once: Avoiding the Awkward

Although dating multiple people at one time has become a much more accepted route with the popularity of online dating (and therefore the necessity of meeting each person you might have a connection with in person to see if there’s anything there), there seem to be a lot of differing opinions and questions about it:

- Do you fully disclose how many dates you have this week with the person you’re on a date with tonight?

- What constitutes “dating”? Definitions range, depending on the person, from meeting for coffee to it being a term only applied to a monogamous “will you be my girlfriend?” pre-marriage coupledom.

- Are multiples an efficient way to figure out who’s best for you or is it an ultimate playboy lifestyle where you can get your cake and eat it too?

Navigating the emotional minefields of each separate person in your personal black book takes skill, grace and tact — and a giant heap of communication.

I think that most of us assume that until there’s an actual conversation about where we stand in a dating situation, as long as we’re treating the other person with respect, what we do in our time away from them is our business. As for when to bring up the conversation (similar to my post about the DTR ) having a talk with someone becomes necessary when you can a) sense that they’re thinking that they’re the only one you’re dating or b) when you sense that you’re not the only one they’re dating and you’re interested in going in that direction. Ultimately, we’re all responsible for our own feelings and actions, so while it’s not your responsibility to constantly monitor how the other person may or may not be feeling, it’s still a good idea to have their thoughts in mind so that you don’t inadvertently hurt them — no one likes being a jerk. This is especially true when sex comes into play, because oftentimes there’s going to be more (and sometimes unpredictable) emotion involved.

All that said, while I think honesty and integrity in dating are extremely important, I do not subscribe to the theory that you should mention on the first date that you’re currently also dating sixteen other people. This looks like bragging, despite the place of honesty it’s coming from. A much more realistic and non-jackass way to go about discussing your (or their) other activities is to wait until you sense that either one of you is not on the same page: “Hey - I like you and I’d like to keep hanging out to see where this goes, but I want to make sure we’re on the same page so that neither one of us gets hurt.”

Basically, whether your goal is to get as much ass as possible or you’re looking for your soulmate in a time-efficient manner, being sensitive to what the people you’re dating are feeling is key. Assuming that they’re on the same page is fine for a while, but as soon as emotions start getting involved, it’s important to let them know where you stand and what your plans are so that no one gets inadvertently hurt. If they’re down to continue, rock on. If they’re not, they can bail.

Yours in time-efficiency and awkward-avoidance, S