6 Casual Dating Tips for Average Joes

Dear Jamie,

I wasn’t one of the lucky ones in the looks lottery. I have a big nose, pock marks from childhood acne, and that very pale pasty and sometimes ruddy skin tone no one likes. I did ok though, met a woman I had a lot in common with and we fell madly in love. She found me attractive, and we had a good life.

Unfortunately, she passed away a few years ago. I’m ready to start dating again, but not quite ready to look for a serious relationship, so I’m thinking of trying out casual sex for a while. But I’m a six at best, and have the widow’s peak balding pattern thing going on now, plus I’m in my mid-forties. I’m wondering if you have any tips for the regular guy on how to increase our sex appeal? – Average Joe

Can Average Guys Find Hot Hookups?

Dear Joe,

I was going to chastise you for the least attractive quality of all—feeling sorry for yourself about your appearance is never a good look. Honesty is one thing, or just being candid about the truth, but a pity party is always an ugly thing.

So that’s the first thing on my list for guys in your situation—if you got the short end of the stick in the hot lottery, you can start to increase your sex appeal by laying off the crocodile tears.

Reading on, I see that maybe that’s not fair. Understanding that’s a woman’s first reaction, however, is something you and other guys need to see, so I left it in. I do have empathy for what you describe because you have suffered a major loss, not just of a partner but of the security and sexual confidence you had there.

You are understandably terrified of facing the dating scene now. Any guy would be, even a ten, so I wanted to go soft on you and acknowledge how your feeling of sexual worth can really take a hit from loss. Going back into the world of dating after a separation, divorce, death, or break up is no easy feat.

Dating again can increase your confidence and help you reconnect to your sexual self. But yes, dating can be challenging. You need to develop a realistic sense of your physical attractiveness—and when I say “realistic,” I don’t just mean coming to terms with the fact that you aren’t twenty years old anymore or that you don’t have a mane—I also mean knowing that being a six is a pretty good deal!

Casual Dating Tips for Average Joes

Ready to jump back into casual dating? Use our Guide to Casual Hookups to meet new partners, and heed the advice below.

Ask a trusted female friend or sister for advice.

You don’t want to be someone else, because you’ll never be able to “wear” him convincingly or get laid. But at the same time, you are probably in a rut. You’re coming off of a period of depression and isolation.

You want some swaps, updates, or something new to present. It might be a new pair of sneakers to wear with your favorite sweater and jeans. It might be updating your do—a full shave can work wonders if you don’t like where your hairline is landing now.

A close girlfriend who loves you, or a sister who cares, can suggest ways to shine that still feel true to you. Just a simple lateral change can work wonders!

Read: How to Increase Your Sex Appeal

Build resilience through rejection.

Dating is fun, but there are landmines.

Don’t take everything personally. Be prepared for rejection, for no responses at times, for fickle dates, for no-shows—the whole nine yards. Take it with a grain of salt.

Read: 4 Ways to Conquer Your Fear of Online Dating Rejection

Friends or family who have long-term experience with online dating can be awesome when helping you navigate the common pitfalls of casual dating.

Have realistic expectations.

If you’re so shallow that you are only looking for a supermodel, you might be one of the average joes who grumbles all the time about never getting laid.

Find beauty in every woman and understand that most women aren’t tens. They are normal, average, everyday women with real bodies, wear and tear, physical illness, and life circumstances—just like you. We all have insecurities.

So remind us of what we know deep down: beauty is more than skin deep, and there’s a full range of beauty.

Read: Don’t Have a Type: The Secret to More Sex

Be attractive in more ways than looks.

Sex appeal is not just about physical looks, but about being interesting, having a love for life, and being passionate and interested in the world. Attraction is about paying attention and listening to the people you come into contact with, being active, being responsible, being empathetic towards the world, being politically engaged or involved in the community, and the list goes on and on.

Read: How Average Joe Gets Laid Every Week

Stay in the present.

Don’t unconsciously beg for sympathy by going on and on about your loss. No one can compete with that. And no one wants to hear about a man’s divorce for hours when contemplating an evening hookup.

It’s fine, sometimes, to mention your life circumstances and motivations in your online dating profiles—we like to date human beings, after all. Some of us may even want to show a newly divorced guy a good time or inspire someone to find life again after a loss, but we sure as hell doesn’t want too much emotional stuff or backwards gazing when we’re hoping to get naked and live in the moment!

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

Focus on fun.

Casual sex is pleasure seeking.

We don’t want so much background about a person that we start to get entwined in their life, and we don’t want to carry many burdens around, because the hookups are temporary and are about escaping from life’s pressures.

We want to meet our sexual needs, and have a good time. Keep things light, funny, and good-natured.

Read: 7 Reasons Women Choose Casual Sex over Relationships

Are you making your way back into the dating scene?

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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