Why Two Dates Aren't Always Better Than One

When two 20-somethings go on a first date, it’s probably safe to assume that one or both parties has other similar outings lined up for later in the week.

After all, the vast majority of first dates won’t work out, and you’d be crazy to cancel on that guy you met at kickball just because your friend’s cousin finally asked you out, and you’d be just as crazy to say no to the cousin just because you’ve been on two dates with the kickball guy, who, now that you think about it, is 27 and still interning on the hill.

There’s nothing morally reprehensible, or skanky, or even just icky about dating multiple people at the same time. There’s nothing wrong with giving a guy your number when you’ve been on a few great dates with a guy from OK Cupid.

If you put yourself out of commission any time a new guy comes up, you might give up a lot for a guy you could lose interest in after a few more dates.

It only becomes an issue after you hit that murky double-digit date mark where you don’t want to DTR, but you’re thinking this is headed toward exclusivity. You hope he’s not seeing anyone else, but you’re not sure, and the impulse to ask is getting harder and harder to ignore.

There are all kinds of ways to overcome this urge to launch into a “where-is-this-going” conversation, which, as we’ve discussed, is a bad idea.

But one of the worst solutions is filling up your free nights with more dates.

It’s not because it’s unfair to the guy or unladylike—it’s because it’s unhealthy for you.

When you’re seeing someone you like and filling your social calendar with guys who asked for your number, you’re using these dates as a way to protect yourself if it doesn’t work out with the guy you like.

Rejection stings each and every time it happens, but when you try to preemptively ease the pain by giving yourself more than enough backup options, what you’re really doing is curing rejection with validation from other people.

The problem with this remedy is that it makes you dependant on what other people think of you. You can’t be happy unless someone else likes you, which is a really inefficient way to find personal satisfaction/contentment. If you can’t feel good about yourself unless someone else is showering you with compliments, you’re going to waste so much time seeking out people who otherwise wouldn’t be worth it.

When your sense of self-worth relies on other people, you’re setting yourself up for unhappiness. People flake out for no reason and lose interest over things you can’t control. The more weight you put on their validation, the bigger the letdown.

When you deliberately line up other dates when things are going well with another guy, you’re also setting yourself up for bad dating habits.

That’s not to say that you shouldn’t go out with a friend of a friend that you’ve met a few times, who seems really great, and who you think might be a better match than your current prospect.

But when you’re handing out your number to anyone who asks and getting drinks with guys who set off warning bells before they even ask you out, you’re establishing a pattern of behavior that sets relationships up to fail. You’re learning to keep your distance, sneak around behind someone’s back,  and stay as far away from monogamy as possible.

We should say that most women don’t have this problem—if anything, some could use a lesson in not getting attached at the drop of a hat.

But for the rest of us, successful relationships usually don’t come from keeping as many options on the table as possible.

And if you stop relying on other people to tell you how great you are, rejection won’t sting as much in the first place.