Dating More Than One Person At Once: The Juggling Act That Is Gen-Y Dating

by John Picciuto

There seems to be an ever-increasing proclivity for Gen-Yers to date more than one person at a time. In principle for the age group I’m talking about, part of me understands the inclination for such an arrangement. It’s a hookup culture we live in and it seems ever more likely that people are looking for more casual types of relationships.

Unfortunately, this leads to some serious headaches when one person within these pseudo relationships catches feelings. So what do you do? How do you decide when or who to choose between two people, and how do you avoid a potential disaster? Here are some tips and thoughts I have on how to handle the juggling act of the casual dating scene and bypassing your likelihood of getting hurt.

First and foremost to me, the number one key to building any semblance of a successful relationship with one person or in this case, many, is communication. This goes beyond messaging them on Facebook, texting them, or hitting someone up on Tinder. We live in a hookup culture. I get that.

I understand that, and accept that. But just because we fall within an age group of people just looking to have fun, doesn’t mean we need to treat people poorly. It’s very easy to be honest and upfront. Take the time to articulate what it is you’re looking for from the beginning and avoid having a Hiroshima level blow up down the road.

The problem that I see is a lot of times, even if someone articulates at the onset of a relationship that he or she looking for something casual, things have a way of growing and morphing into something larger and much deeper.

I think on the whole, meaningless sex on paper makes sense for some people. But deep down, we crave something more. What starts off as a fun, non-intimate fling often grows into something more, which is why communication is obviously key.

If you’re dating more than one person at a time and this has gone on for a while, maybe, just maybe, it’s gotten to the point where you need to make a choice.

Look, if you’re hell bent on dating around and doing your own thing, you don’t necessarily have to make a clear decision on whether you date someone exclusively or not. But from experience, if you don’t put up or shut up, it’s likely that you’re going to lose one, if not both, of the people you’re seeing.

If you’re dating two girls at once, and they both seem to be getting pretty serious, it’s time you make a decision. Investing a significant amount of time in more than one person can be tricky, and with the holidays coming up what are you going to do? One gets Thanksgiving the other Christmas? No, I don’t think so.

At the end of the day, you have to let it be known what exactly it is you’re looking for in a relationship. Unfortunately, in a world with ever-increasing awareness of one’s relationship status on Facebook and every other social media site, we’re inclined to immediately label relationships.

Be honest with the people you’re seeing. If you’re not looking for anything serious, let that be known and continue to press the point. Labels don’t always solve problems and at times people jump to slap a label on something that truly is only a hookup. Don’t rush. Be smart. If it’s just sex, it’s just sex. If it feels like it’s growing into something more, maybe it’s time you talk about things don’t you think?

Communicating what it is you’re looking for and what you ultimately want is the first step to avoiding a disaster. Truthfully, there’s nothing worse than dating someone for a while only to find out months down the road that he or she was never looking for anything serious. Talking about what you’re looking for at the onset of a hookup can stave off a huge blow up later.

Inevitably, every one of these juggling acts comes to an end, and eventually, you’re going to drop one of your balls if not both (pun intended). So be upfront, be honest, and articulate exactly what it is you’re looking for and what you want. This is the easiest way to avoid drama and find someone who’s looking for the same relationship you are.

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