Playing Both Sides: The Realities of Dating Two Men at The Same Time


We’ve all been there. We’re single, looking for a new guy to talk to and you finally find one. You exchange numbers, start texting, go on a few dates and everything is great. Nothing too serious has happened yet, so you keep your Tinder account and keep swiping when suddenly you get a match! You both talk, exchange numbers, talk throughout the day, go on a few dates and everything is great…. Except you’re still dating that first guy…. And neither of them know about each other. You didn’t mean to date two guys at once, but you like the extra support you have and you know you’ll cut things off with one when you feel it’s not working anymore. But in the meantime, what are you in for?

You’ll Mix Up Their Names

It’s bound to happen. You’ll be talking to Andre and accidentally call him Chad. When this happens you can easily blame it on a slip of the tongue, but if you call out Chad’s name while having sex with Andre, you’re going to have to spill the beans.

You’ll Start to Wonder If They’re Dating Other Women

All this running around to see both guys is going to eventually make you feel paranoid. “What if they’re dating another woman?” This is all part of the guilt you may (or may not) feel when you have two secret relationships. You’ll start getting paranoid when they get a text or mention a female coworker.

They’ll Both Have Amazing Qualities That the Other Doesn’t Have

If only choosing one was so easy. Guy #1 is there for you emotionally, he cooks you dinner, and gives you sensual massages. You can really see yourself in a nice home with Guy #1 and rescuing a shaggy dog named Scooter from the shelter. But then there’s Guy #2. Guy #2 excites you. The sex is amazing and you have fun together. Things are never the same and always new. He may not be the most stable person, but you know you’ll never be bored with him. If only Guy #1 and Guy #2 could merge into one super man.

They Will Text You While You’re Out with the Other One

Your brunch date with Brad is bound to get interrupted by a “What do you want to do today?” text from John. And your dinner date with John is bound to get interrupted from a booty call text from Brad. It’s not like you can just ignore a text, because then they’ll get suspicious and angry with you, but at the same time you can’t just text another dude in front of the dude you’re on a date with. Saying you’re with your girlfriends won’t work if they’re a mutual friend.

You’ll Go Through A Lot of Condoms

Two dudes mean two times the sex, or maybe just the same amount of sex but twice the sex drive. Just because you’ve already had sex 3 times this week doesn’t mean he has. Too keep them from getting suspicious you’ll need to make sure there are plenty of condoms to go around, I you’re having sex 3 times a week with Guy #1 and Guy #2 notices that you had 10 last week but only 4 this week, he’s going to know another man has been here. Plus, you’ll want to make sure you don’t run out for personal reasons.

You’ll Be Debating on Which One to Choose

You don’t want to be dating two guys at once and stringing them along. You know you’ll eventually have to make a decision on who you want to choose as your official man. One you can bring home to Grandma’s house and take as your plus on to your cousin’s wedding, but you’ll live in a constant state of “which one is the right one?” You don’t want to choose Guy #1 only to realize you should have picked Guy #2. The longer you wait to choose, the more likely it is that they’ll find out what’s happening and you’ll end up losing them both.