Hookup Help

How to Get Back Into the Dating Game

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Has it been a long time since you dated? Are you new to online dating? You are not alone.

Read a letter from a reader followed by tips on how to get back into dating after a break.

Dear Jamie,

It’s been a few years for me—six to be precise—following a messy divorce, then being too scared to date casually during the pandemic. I’m long over the wife and married life now, and am not thinking about serious relationships just yet. I want to play first and explore my sexuality. I was a faithful guy, so it has been 21 years since I have slept with anyone other than my wife! I’m a bit rusty. 

I also don’t have any experience with online dating and am not sure I can keep up with the rules and all the apps just to get some! But how else can I meet women? And how can I come across as a little more hip or up to date? I don’t want to come across as a player. I would like to try out kinky fun too, but the special sites for kinky dating seem way too intimidating and intense… and I’m just looking to be, well, playful in bed and not full-on fetish life. 

Specifically, I want to sleep with a few different women, also experiment with threesomes and a bit of bondage maybe, that kind of thing. I’m not bad looking, nothing special but a decent build and look after myself. I think women find me attractive an average amount of the time. It’s more about confidence after a long dry spell and how to go about getting back out there. Thank you kindly for any advice you can give. – Gregory, 48

Congrats, Gregory, on the wonderful adventures ahead! So glad you are embarking on a new journey after taking the time you needed to. The truth is lots of women looking for hookups are looking for “playful” encounters—nothing too serious, affectionate, and fun—with a nice guy like yourself.

Read: The Truth about Women and Casual Sex

I generally advise people to be honest and be themselves. You don’t have to pretend you’re used to hookups or that you’re a hardcore kinkster. There are lots of women who are looking to experiment too. 

Here are practical tips for getting back into the dating game after a dry spell—tips that can work for all of you out there looking to get back into the pool.

How to Get Back into Dating

Get advice from a trusted sister or girlfriend.

Is there a woman who loves you, but not “in that way”? If you have a candid friendship with someone, start there with a little coaching about what to tweak.

You need to know if your cologne is too strong, if you need a new sweater, and what pictures are best for a profile. Ask her to help you create a simple profile and choose a decent haircut. Ask her for the hard truth about any annoying habits or turnoffs. 

Just to be clear, I don’t mean a big overhaul when you get back into dating. More of a fine-tuning, from a woman who loves you the way you are, and who cares whether you get a great date. You may not have particular friend in your life, but if you do, it doesn’t hurt to ask for some assistance. Think of the women you get along with best—a sister, a co-worker, a friend.

Read: How to Survive a Dating Dry Spell

Update who you already are.

You want to freshen things up and switch gears without losing your sense of self. Whether you are a sporty guy, suit guy, a suave gentleman, surfer dude, or a big nerd—embrace yourself. Nothing is cornier than playing another guy. But do sex up a little.

The basics of shaving, flossing, and showering are a no-brainer for every possible date. But get a stylish haircut in your personality range, update your cologne, and get a nice shirt.

Read: How to Increase Your Sex Appeal

Part of freshening up is your new lease on life as well—doing things to engage your mind and body—expand your horizons—is essential. Think about those things outside of sex that you’ve always wanted to do and sign up for them. Not only will you meet new people that way, but you will also feel new and empowered with the kind of confidence you’re looking for.

Take a leap of faith.

If you’re just getting back into dating but you’re not sure what you want or how to go about it, don’t be so choosy.

Some guys are picky, overthinking every opportunity to death. So what if she doesn’t look like your ex, or your ideal dream girl. Open your heart and mind to any connections that come through, in real life or in online dating. How many people say their sexiest encounters and most intimate partners were “just my type, exactly as I planned and fantasized”? Not many.

Read: Why You Should Date Outside Your Type

For casual sex, the backstory is less important than if you’re looking for a lifelong lover, anyways. Play and see where it goes when someone connects with you. 

Being extra finicky or just unsure isn’t so much about a guy not finding any women attractive—most guys will be happy with an average woman and happily dream of a porn star or movie star, after all. It’s more about putting it off and avoiding the very connections you want to be making! Ask a wider range of women to connect if you’re not getting the call back from a selected few.

Read: 4 Signs You’re Ready to Date After a Breakup

Be honest…to an extent.

I think it’s preferable to let women know you’re a little rusty and that it’s nothing to be shy about. It’s even a little sexy.

Be careful, though, about divulging too much. Don’t trash your ex, say anything mean or whiny. It’s okay to be a bit vulnerable, but not to put yourself at risk of manipulation or being played. Sometimes men can share their pain a bit too easily—the opposite of the type of guy who never talks about his feelings. I think it’s great to be open, but that will be down the road when you’re looking for something more intimate.

For casual encounters, you don’t need to go into too much. In other words, you have nothing to hide but don’t need to wave your rusty status like a flag either. Just saying you are divorced, it’s “been a while,” and that you are looking for new experiences is perfect.

Read: 5 Tips for Dating after a Long-Term Relationship

Are you just getting back into dating? Please share your experience!

Hookup Help is a Q&A series. If you want advice or a woman’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.

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