6 Tips For Dating In The Big City: A Guide For Newcomers

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When you come from a small town, or from the peaceful, leafy suburbs of Bumblefuck, Western Australia (like I did), dating in  any big, cosmopolitan city can be a strange and troubling experience. It can also be a lot of fun. Here are my six rules for getting the most out of dating in in the city and staying sane and positive while you’re at it.

1. Date Online: I’m not saying you shouldn’t be open to meeting people in more traditional ways, but I am also saying you should be dating online. Maybe there’s still a bit of a stigma attached to online dating where you’re from, but in the city, it’s de rigueur. Serious relationship seekers are on Match.com, casual sex fiends are on Tinder, and OKCupid has a little of everything. But everyone is on something. For dudes, there’s an extra plus. For some reason, a lot of guys have trouble keeping their drooly creepiness under wraps online. Any woman on Tinder or OKCupid gets a daily deluge of inappropriate, explicit and weirdly detailed sexual messages. That’s not fun for them.

On the plus side though, dudes, if you’re able to reign in your creepy id for long enough type an IM, you’re already at a huge advantage. Keep that shit courtly and you will see results. She’s got a great picture? Can’t stop thinking about sliding your fat cock between her tits or whatever it is? That’s good! Everyone should have an interest! But keep that information close to the vest at least for a little while, okay? Guys, this shouldn’t be hard.

2. Be Up For Shit:  I grew up in a sleepy Australian suburb. Your mileage may vary, but unless you were raised in a strange commune, a big city is probably more sexually permissive than wherever you’ve come from. People are more likely to tell you exactly what they want from you in bed. This can be a steep adjustment but, on the whole, I’ve found it to be a very positive one. It’s great not to have to guess at what turns somebody on. It’s also more likely you’ll be called on to step outside your sexual comfort zone a little. Obviously you don’t have to do anything that really makes you uncomfortable, but it’s great to keep an open mind. You might find all kinds of fun in unexpected places.

3. But Only Be Up For Safe Shit: I’m all for sexual permissiveness but that doesn’t mean being unsafe. In the last couple of months, I’ve heard a bunch of stories from lady friends about Tinder hookups trying to weasel out of condom use. There’s a pattern to these stories. After a night of flirting and drinking and making out and more drinking and going back to someone’s apartment and foreplay, you reach a point of momentum at which not having sex becomes almost unthinkable. It’s only then that he brings up the condom thing: “Oh, by the way, I can’t use a condom because [whatever].”

This isn’t by accident, it’s coercion, designed to make you feel like you either have to accept an unreasonable risk or take responsibility for “ruining the moment.”

Guys: don’t do this. Just don’t. Ladies: recognize this kind of bullshit for what it is and don’t accept it.

4. Don’t Be Jealous: I never really had to have the exclusivity talk where I’m from. If you were sleeping with someone, the default position was that you were sleeping only with them. In the city, it’s the other way around. The person you really like is sleeping with whoever they want until you both agree otherwise. This can be a tricky adjustment — painful to the heart and punishing to the ego. Try not to let jealousy ruin your dating experience. If exclusivity is a priority for you, be upfront about what you need. If your partner can’t accommodate you, it wasn’t going to work, anyway.

5. Be Sincere: Everyone knows that dating is crazy and that has led to a strange kind of relationship tourism. A Carrie Bradshaw syndrome, if you will. “I did it for the story” is a real reason for crazy behavior these days, apparently. More than once, I’ve found myself trying to put my finger on what was a little off about a date and thought: This girl actually wants me to do something fucked up! That’s difficult to prove and I have nothing to quote except the vibe, but I believe this happens. Bad writers think they need crazy relationship stories and some people just believe they aren’t proper grownups unless they’ve gone through a hazing process of strange sex.

By all means, be a writer, be a comic, be whatever. It’s your right to turn your experiences into art. At The Frisky, we do it all the time. But approach each date with a sincere intention to make some kind of connection with a person. The wild stuff will happen without you looking for it. Your date is a human being, not fodder for your blog. Don’t do things you don’t like with someone you think is gross just to have a crazy story. That story won’t make you sound worldly, it will make you sound gross.

6. Embrace The Mess: You will have disastrous dates. You will have awkward and sometimes unpleasant sex. You will face rejection and heartbreak. Isn’t that great? Can’t you just feel yourself becoming a more experienced and well-rounded human being? Dating in a big city is a grand adventure. It’s good to have an end goal in mind, but don’t let that stop you from valuing each experience along the way for it’s own sake — even the bad ones. Oh, and be nice. This is hard for everyone.

Kale Bogdanovs is a standup comic and also Jessica’s husband. Follow him on Twitter.

[Image of the Chicago skyline via Shutterstock]

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