How To Make Hooking Up For The First Time Less Awkward

Dear Love Drive, 

I need advice on how to make hooking up with someone less awkward. 

I’ve gotten some matches on Tinder that are only available for hooking up, but I don’t know how to approach the situation.

I’ve done one night stands before, but I’ve never driven over to someone’s house for the sole intention of hooking up.

How do I go about it without the situation being awkward? I have a major tendency to overthink every situation.

What are some tips on not being nervous and just enjoying the moment?

Just a hookup, 25 M

Lucky you. It sounds like you’ve met some people on Tinder that you want to be hooking up with, but you’re scared that it’ll be too awkward. 

The Uncomfortable Reality of Hooking Up

Planning a sex date with a complete stranger and following through with it is going to be a bit awkward, at first. And that’s OK. 

A sex date is like any other date, except that you’ve both decided ahead of time and discussed the fact that you’re meeting up for the expressed purpose of hooking up. 

I’ve never gone on a date that wasn’t a little bit awkward at first. The awkwardness goes away once we’ve found some common ground and found some flow in our conversation.

The common interest in your case, however, is that you both want to have sex. That’s a pretty damn good place to start by the way. 

It’s great that you’re both sex-positive enough (or horny enough) to realize that there’s nothing wrong with hooking up on the first date, even if you’re complete strangers.  

Listen to the hooking up episode

6 Ways to Make Hooking Up Less Awkward

1. It’s Going To Be Awkward​

Don’t worry about it. It’ll be awkward, and the awkwardness will go away, especially when your sexual arousal takes over. 

Awkwardness is temporary. Learn to recognize it. I’ve found that naming the awkwardness can be helpful. 

“Gosh, I’m feeling a bit awkward here, and at the same time I’m really happy that we got together.”

2. Be Clear As Glass

Be crystal clear with your potential partner before heading over that this is a sex date. The clearer you can be, the better. You don’t want to walk into a situation where one person thinks it’s a sex date and the other thinks it’s a movie date.

There’s nothing wrong with being upfront. This situation requires it. 

“I’m looking forward to coming over, and want to make sure we’re on the same page about us both wanting to have sex tonight. I also want to express that we’re both free to change our mind at any time. Just because we both want to have sex doesn’t mean things can’t change.”

​3. Have No Expectations

No matter how horny you both might be, everything can change.

Your partner might decide they’re not as attracted to you as they thought they were. You might realize that while you want to have sex, this isn’t the kind of experience you’re looking to have. 

Sexual arousal can lead to lowered inhibitions and drive us to act in ways we’re not used to acting. It’s OK for you or your partner to change your minds about having sex. 

“I’m sorry. I know we had planned on having sex but on second thought, I’m actually not up for it tonight. Would you like to cuddle/watch a movie/go out for a drink instead?”

4. Own It

Yea. You’re going over to have a sex date with a stranger. Badass. Two consenting adults having sex to enjoy themselves is rad. There’s nothing wrong with that.

Being confident in your choice of having casual sex with a stranger will result in your looking and acting more confident. 

There’s nothing to be ashamed of here. 

5. Jump Right In

I tend to overthink situations. I deliberated for 3 hours before having my first threesome. I wish I’d jumped right in; it would have been easier on everyone. 

After the small talk, jump right in. You’re both there for the same reason, the longer you wait, the more awkward it might be. 

“I’m so excited to be here. Should we start by kissing and getting naked? Or do you have something else you’d rather start with?”

​

Make sex collaborative. It’s a two (or more) person activity so check in with your partner, often, about how they’re feeling and what they’d like to do. 

6. Continuously Check In

Don’t make any assumptions about what kind of sex you’re going to be having. Check in with your partner at every step of the way. As new partners, having a discussion about what you each want and checking in along the way will help make sure the sex date is fun for everyone.  

These are all direct ways of either expressing your desires or checking in with your partner. Communicating about sex is a part of having sex, and it’s a turn on. 

“What kind of sex would you like to have? I’m interested in oral, penetration, massage, and making out. I’m not comfortable with anything above a little spanking. Name-calling and choking are a hard no for me.”

“I think you’re incredibly beautiful and I would love to go down on you. Is that something you’d like?”

“Would you like me to continue?”

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​Did you know that talking about sex will make you better at sex?

Sex is supposed to be fun, and a little bit awkward. If you remember that you’re both hooking up to bring pleasure to each other, you can’t go wrong. Now go have that sex date already!

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