Hookup Help: Rising above Dating Rejection

Q: Dear Jenny. I have to say… I’m at an all-time low in the dating, hookup, relationship, and whatever else you want to put in that list – all things women, basically! I just can’t seem to catch a break and it’s affecting my self-esteem. I haven’t had a girlfriend in years, and I haven’t wanted one. I enjoy playing the field, having sex with a variety of women, and chasing after that holy grail of a threesome… but lately it seems I can’t even get a one night stand to save my life. I feel like women everywhere have a communal axe to grind against me… like there’s some secret society where they’ve decided that player Brad is to be vexed at every turn – in the bars, at the park, and my online dating site. I’ve always thought I was all-right looking, I’m not an asshole, and I make pretty good money. How can I get past this? Feeling desperate enough to hire an escort. -Brad

A: Hi Brad. No one – not even the hottest of the hot guys, smooth as silk snake charmers – can ride the wave of lusty hookups without crashing once in a while. Because you haven’t been in a relationship for a long time, you may have settled into a routine when it comes to flirting and trying to pick up a girl, whether that’s in a bar face-to-face or online via instant messaging or texting. If you’re using the same-old same-old tricks to get a woman’s attention; she may very well pick up on this. We can smell a player a mile away. Shake it up; use a different approach.

You’re name hasn’t come up in the secret society… just kidding! But I know what you mean; a dating dry spell can rock a person’s confidence, and I see that in your self-description. You should be saying things like “I’m a gentleman”, not “I’m not an asshole” and “I have a good job”, rather than “I make pretty good money.” See the difference: one is positive while the other places emphasis on the negative. It might be time to have a look through your online dating profile for revisions.

One more suggestion: take a dating break. You say what?!?! …give up the quest for the holy grail? Believe me, Brad; it’s not going anywhere. During this hiatus, take the time to focus on YOU. Pursue your passions, whatever they may be; or gain a new skill. And when you return to the dating jungle, you’ll find that women love men who DO things and have skills, not just in the bedroom… but those are much appreciated, too!

Chin up, Brad… and good luck on your quest!

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 HERE, and who knows, you may appear in the next Hookupland newsletter. -xo Jenny

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