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How To Make Hooking Up For The First Time Less Awkward

Shaun Galanos

October 11, 2018

Seven tips and scripts to help you enjoy the hookup

How to Make Hooking Up Less Awkward

People want to hook up but don’t want the awkwardness that might come with it — I get it.

I’ve had my fair share of awkward hookups in my day, and while I don’t regret any of them, I wish some of those experiences would have been more comfortable and less nerve-wracking.

And there’s always the risk that it’ll be awkward because, for the most part, sex is awkward, especially with a new partner. You’re essentially going to grind your genitals together in a way that hopefully makes you both feel good. Sounds pretty awkward to me.

Therapist, sex columnist, and past guest of The Love Drive podcast, Yana-Tallon Hicks describes hookups as “uniquely separate from a relationship in that they are […]casual or short term and require minimal official commitment between the people involved.”

And it’s that lack of commitment and casualness of connection that can contribute to a hookup’s awkwardness. You might be more self-conscious and more nervous around that new person, which might lead you to act in ways you usually wouldn’t.

Generally, the more you have sex with someone, the more comfortable you become, which can go a long way to lessen the awkwardness you might feel together.

The Uncomfortable Reality of Hooking Up

A research paper on the definitions of hooking up found that “hooking up generally refers to having sex; however, many others indicated that they refer to something less than intercourse when they say hooking up. Hooking up is a means for experiencing casual sexual encounters, but it is also a means for beginning relationships.”

While my article won’t shed light on the broader implications of hookup culture and its effects on relationship building, it’s important to note that hooking up serves various purposes, and it’s here to stay.

Some folks hook up because they don’t want the commitment that a more established relationship requires, or they’ll hookup as a way to enter in a relationship, re-negotiating the terms of that relationship when they start developing feelings for their partner.

Hooking up can be a euphemism for casual sex, including penetrative sex. People can refer to hookups as any sexual activity that folks can engage in, but that explicitly excludes penetrative sex.

Regardless of whether your date turns into a hookup, or you’re planning a hookup with someone you met online through a hookup or dating app, there’s a high chance that it might be awkward — because people are awkward!

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. And the same applies to hookups.

Here are seven ways to find a little flow in your hookup and make the whole experience less nerve-wracking and more enjoyable.

Seven Ways to Make Hooking Up Less Awkward

1. Accept That It’ll Be Awkward

Hooking up with a stranger will most probably be awkward, and the awkwardness will go away, especially when your sexual arousal takes over.

The awkwardness you feel standing in front of a person you barely know is understandable and temporary. Accept that it’s a natural part of the process and that’s it’s perfectly understandable to feel awkward.

And remember why you’re here: because you’ve both expressed interest in wanting to have sex. Which might be motivation enough to walk through your fear of being awkward.

2. Name The Awkwardness

Often, I’ve found that naming the awkwardness can dissipate that nervous energy that might surround a first-time hookup with someone.

Author and Psychiatrist Dr. Daniel Siegel developed a strategy called “Name It To Tame It” to help children deal with their uncomfortable and unpleasant emotions. Naming the feelings allows us to get some space from it and speeds up the processing phase of moving through emotions.

Naming the awkwardness will help dissipate it, and you might be surprised to find out that your hookup partner might be feeling a bit of awkwardness as well.

“Gosh, I’m feeling a bit awkward here, and at the same time, I’m thrilled that we got together. How are you feeling right now?”

Remember, it’s OK to talk about the fact that you’re about to have sex. People who talk about sex have better, more connected sex. Just because you’re hooking up with a new person, it doesn’t mean that you can’t have exciting and intimate sex.

3. Be Transparent

A Teen Vogue article explored Research from Confi, a digital health startup founded at Harvard Business School, and found that “45% of college-aged men expect to have penetrative sex if they take someone home after a party, while only 31% of women expect the same.”

Don’t rely on expectations or assumptions to drive your hookup. Check with your partner to make sure you’re both on the same page.

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

There’s nothing wrong with being upfront; this situation requires it. If you’ve made plans ahead of time to hookup, confirm them.

“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 minds at any time. Just because we both want to have sex doesn’t mean things can’t change.”

Don’t worry; checking in about your desires won’t kill the mood. The mood isn’t so fickle that a quick text message will destroy it; it’ll probably lead to a sexier experience because now everyone knows what’s coming, and there’s something sexy about transparency.

​4. 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 not up for it tonight. Would you like to cuddle/watch a movie/go out for a drink instead?”

And if your partner changes their mind about you, it’s OK to express disappointment.

“Oh, wow. I’m a bit disappointed. I was looking forward to having sex with you tonight. And, I understand that you’re no longer in the mood. I think watching a movie could be a good consolation prize!”

And if you’d prefer to leave, that’s fine too. There’s no point in staying if you don’t want to be there.

“Oh, wow. I’m a bit disappointed. I was looking forward to having sex with you tonight. And, I understand that you’re no longer in the mood. I think I’d rather go home than watch a movie. Thanks for offering an alternative. Take care of yourself.”

Will this be awkward? 100%. Very awkward. And that’s OK. I’d rather you feel awkward than to do something you don’t want to do.

5. Own It

Yea. You’re going to hook up 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. Enjoy the shit out of that hookup; you deserve to be happy about it.

6. Jump Right In

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

After the small talk and the discussion about sexual health and sexual health practices, 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. Now that we talked about sexual health, 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.

7. Continuously Check In

Don’t make assumptions about the kind of sex you’re going to have — 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 hookup stays fun for everyone.

Here are a few 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 hard nos for me.”

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

“I’d love it if we took a bath together; it always helps get me in the mood. Would you like to join me?

“I want to make sure this feels good to you, so if there’s anything I can do to make this feel even better for you, please tell me.”

Be More Ethical and Transparent

The strategies and tools described in this article will lead to a more ethical hookup, and a more ethical hookup feels better for everyone involved.

Being honest about your needs and desires, owning your sexuality, and checking in with your partner often makes for a more empowered, transparent, and collaborative sexual experience.

This new empowered and transparent mindset can lead to less awkward hookups because everyone feels better about the sex that ensues.

Oh, and the more you do anything, the better you’ll be at it. That concept applies to life in general and certainly applies to hooking up as well.

So, what’s holding you back? If a hookup is what you’re after and you’re tired of the awkwardness, then get to work.

Shaun Galanos

Shaun Galanos is a love coach and course creator. He teaches communication and intimacy tools for better relationships and more love.



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