Why Is Setting Up A Date So Awkward?

You haven’t experienced true awkwardness until you start seriously dating. There are too many ways to potentially embarrass yourself, and it’s the worst. But sometimes the awkward stuff happens before you’ve even gone on the date at all, while you’re still trying to make plans.

When he sends you a weird ass response.

You’ve been chatting with this guy online for a few hours/a few days/however long you need until you feel comfortable. You seem to get each other’s sense of humor (at least through the Internet) and you ask him out. But instead of saying yes the way you expect, he responds really weirdly. He says he’s going out of town for the next two weeks or claims he’s working on a project right now and can’t commit to a date.

When he wants to know where you live.

It’s hard to keep things private these days thanks to our collective social media obsession but one thing you should never share when chatting online is your address. But when you schedule a date, he asks where you live. It’s super awkward because you know he’s probably just asking to pick a bar (or you hope that’s why he’s asking), but you don’t want to be too specific.

When you realize you both live in the same neighborhood.

This guy is still a total stranger at this point but when you suggest a bar in your area, he says he lives in the area. Which is your area, too. Oops.

When you let him know you’re free all week.

Sure, you’re technically supposed to play hard to get and never let a guy know how truly available you are. But you like him (or at least you think you like him) so you figure, why not admit that your social schedule is pretty open right now. Things get awkward fast because then he says he’s only got one free night.

When you don’t like his suggestion.

You’re trying to be less controlling about where you on first dates, you really are. But did he have to suggest a restaurant that’s halfway across town? It’s going to take at least an hour to get there and you don’t even know him yet. You try to politely suggest another place, but then you just look super picky. It’s a mess.

When you realize you double-booked.

Your best friend has been asking you to see the latest chick flick for weeks and you finally made a plan… it just happens to be the same evening next week that you’ve agreed to meet this guy. What’s a girl to do: risk telling him that you’re super forgetful or pretend a work emergency came up?

When you’re not sure if it’s dinner or just drinks.

This is so awkward because if you say you just want to meet for a drink, he might get kind of offended, but you don’t always want to sit through an entire meal with a stranger. If you’re meeting after work on a weeknight, meeting at 6 or 7 p.m. could mean a few beers or burgers. It’s tricky.

When he never confirms.

This isn’t quite the same as ghosting or being rejected but it’s in the same crappy behavior category. Sometimes you make a plan but it seems super vague. When you follow up a few days later or the day of the date, you get total radio silence. Looks like you’re not going out after all.

When you totally regret saying yes.

Sometimes the worst happens before you’ve even set foot in the bar or restaurant you go to. You’ve agreed to a date and then this guy starts spamming your OKCupid inbox or texting you like there’s no tomorrow. Sigh. Looks like it’s time to cancel and try to find someone else (again).

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