Rules for First-Time Hookups

Q: Dear Holly. I first want to set the record straight, and explain that I’m not a player. I’ve had two back-to-back, long-term relationships and now I’m single and totally need a break.

Meet sexy single women now at!

It’s been two months and while I don’t want a relationship, I do want sex. My buddies got me to join a dating site, but I’ve never even had a one-night stand, so I feel very awkward. How and when do I tell women that I don’t want anything serious? Tim

A: Hi Tim. You sound sweet, and I’m sorry your two relationships didn’t work out. 

First off, you don’t have to feel awkward about only looking for casual sex. Many men, and women, are only interested in hooking up for a variety of reasons—they just got out of a serious relationship, they don’t have the time to devote to anything more, they love variety, or they are polyamorous.

I’m a big believer in being up front about what you’re looking for on your dating profile, otherwise you end up explaining later in an awkward situation. It’s also okay to say that you’ve just come out of two serious relationships, because it shares the fact that you’re a guy who is capable of committing, but one who probably isn’t ready to again—at least not now (this information will put you above the regular player.)

One thing to note is that just because you’re only looking for sex, women still want to be treated like ladies. Most women who are looking for casual sex, still want and need some wooing beforehand. Plan a fun date, pick up the tab, and be a gentleman. And understand you may not get laid on the first date.

Another tip: Bring your A-game to every hookup. You may not think you want a relationship, but you may just meet that special someone while sowing your wild oats. And a hot hookup has the possibility of turning into a friend with benefits. Good sexual chemistry is hard to find.

Online dating isn’t for the faint of heart. It’s a learning curve for newbies, and can take a little getting used to it. Don’t let rejection and unanswered messages deter you. Building dating confidence takes practice.

Share your early online dating experiences in the comments!

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly 

Ready to Find Local Hookups?

Explore the Best Hookup Sites for Getting Laid in 2022.

Find Hookups Now

Tell us what you think

Notify of
Inline Feedbacks
View all comments