Playing Both Sides: The Realities Of Dating Two Men At The Same Time

By Gigi Engle

We all want to find that perfect guy. We're all looking for love: the big kind, the one that will change the world as we know it.

We spend so much of our time waiting, searching, and going through the motions of dating until we find what we're looking for.

Unfortunately, dating isn't always cut and dried. When it rains, it pours -- sometimes.

It's happened to many a gal. The situation feels hopeless until, suddenly, you're on a great first date, and that turns into a second.

The relationship blossoms. But you keep your options open; you commit to a date with someone else ... an  that guy is equally amazing.

You find yourself dating both boys. Hell, why not? You're only young once!

It doesn't seem like a big deal at first. You aren't that serious about either of them. You tell yourself, “It's okay. I'll know when my heart tells me which one of these guys is the right one. I'll come to those crossroads and everything will make sense.”

Yet, without even realizing it, you may suddenly find yourself getting serious about both guys.

Here you are, time flying by, and you haven't been able to choose. You know you should, but you just can't bring yourself to commit.

You feel like Mandy Moore's character in “Because I Said So": hopelessly pulled between the gorgeous musician and the stable, sexy millionaire.

What if you choose wrong? What if you THINK one of the guys is right for you -- but he's really not? What if you miss out on the love of your life?

What IF?!

When two guys are vying for your love, you may feel like the ultimate catch, but you'll end up the ultimate loser.

Your indecision is a cruel trick played by the universe. You've spent so much time being a single girl -- only to be dealt two different aces at once.

This hardly seems fair to you -- and to the two men you're seeing.

You like different qualities in both guys.

The two of them are so different, but both have qualities that spark your interest.

One of them may have the best sense of humor; the other may be incredibly witty and smart. One may have the best butt; the other may have an impressive beard. (Hey, aesthetics matter to girls, too).

When you're seeing two guys at the same time, they're rarely similar. That's what makes the situation attractive: They're great in opposite (yet equal) ways.

The guilt is so real.

You feel like an actress in your own life. You're playing the perfect girlfriend in two different relationships. You're wracked with guilt.

You like both men so much, but you can't bring yourself to pick just one. This makes you want to cry.

At the same time, you're so incredibly happy to have two people who make you feel so good. Your shame is palpable, but your indecision will always outweigh any guilt.

You get massive FOMO.

That ever-dreaded plague, the thing that keeps you wrapped up in both relationships: FOMO.

You keep up the charade as long as you possibly can, hoping that the world will decide for you. You're terrified of missing out. You don't want to choose wrong and end up with nothing.

You don't want to look back on this time in your life and think, “Wow, I really messed up when I was so close to finding love.”

You WILL accidentally mix up their names.

It's completely unavoidable. At one point or another, you will call one of your "boyfriends" by the other's name.

Best-case scenario: It happens when you're out and about. You can backtrack immediately and do serious damage control: “What? Oh, I guess I called you John because my best friend John just texted me. Haha.”

Worse-case scenario: It's while you're having sex. Then you're f*cked. And not in a good way.

It's exhausting.

It is straight-up exhausting to date two people at once. I mean, it's hard enough to make the time to see one person, let alone two.

You end up so overwhelmed as you try to balance your evenings between your boyfriends -- AND make time for your friends.

It seems like more trouble than it's worth.

You're constantly thinking about the future.

You know you have to choose eventually. It's ever-present in the back of your mind. It's a little voice whispering, “You need to pick one. You can't go on like this. They're going to find out.”

You try to picture life with just one boy, but you can't. The guy you're with at any given moment will be the one you like the most. You are always flip-flopping back and forth.

You're constantly tangling yourself in a web of lies.

You become the biggest liar in the entire world. You find yourself making up all kinds of ridiculous fabrications to keep both the guys separated from each other.

One boyfriend thinks you were with your sister last night, so you fabricate anecdotes from your evening together and warn your sister in case he asks. It becomes impossible to keep your lies straight.

You inevitably ruin both relationships.

If you don't come to a decision (AND QUICKLY), both relationships will get destroyed. Eventually, all of the lies and the sneaking around will catch up to you.

Within moments, your whole romantic life implodes, leaving you sad and alone.

Everything sucks; you had two amazing guys, and now you've ended up with nothing. You wanted to have your cake and eat it, too. But you're just going hungry.

You accept your actions and grow from them.

After a lot of tears and heavy guilt, you accept that you handled the situation in all of the wrong ways.

You take responsibility for your actions. You stop blaming the universe and realize that you are the one who messed up.

You promise that you'll be better next time. You swear that this will never happen again. After all, if either of those guys were Mr. Right, you wouldn't have been so conflicted in the first place.