Hey, Daddy! Hooking up is hard to do

Maybe you’re just getting back into dating and sex after a long relationship. Maybe all you ever want is casual sex and booty calls. Either way, Daddy knows hooking up can be oh-so hard to do. 

Hey, Daddy!

What is the deal with Millennials? I was in a 10-year relationship that ended, and I’m back on the dating scene in my 40s, well at least back on the tricking scene. Either things have changed, guys have changed, or I have changed. Maybe all three.

Rather than dating seriously, I thought a little fun with younger guys not ready to settle down would be more my speed. Boy was I wrong. One guy was hot the first time, a mess the second. Another I’m working on but he is proving elusive. There are tons of guys on Grindr, Jackd and Scruff, but they’re too interested in being chatted up.

It’s so much work! I remember my younger, sluttier days with fondness, but I deserve a medal for all the time I put into these men. Was it always this hard? Where do my longtime single friends find the time the energy? I just want the sex without the hassle.

Always Games, I Never Guessed


Life is hard. If you deserve a medal, everyone deserves one, and I don’t do Millennial Participation Medals. You get a GenX Middle Age Cookie – sweet, but not enough to spoil you.

You probably just forgot, but tricking is a full time job. You have to prioritize it, make time for it, and keep at it. Maybe it’s lost its luster because after a real relationship, the payoff doesn’t look as good as it used to – in the pursuit or the prize.

For some guys, the actual trick is less the draw than the chase. Others tell themselves they’re looking for a boyfriend, or play other mind games on themselves to keep up the investment in random flings to avoid the difficult stuff of meaningful engagements. Maybe this used to be you, but you’re older now.

You say you don’t want the hassle, but Millennials are all about the hassle. It’s not their generation, but their age. It’s all new to explore and experiment with flirting, tricking and dating for them, just like you before your long-term relationship.

But I get it. Everybody understands a no-strings orgasm. Sex without any hassle at all is called porn.


Hey, Daddy!

I’m 25 and love a hookup. I’m not interested in playing house but playing the field. How can I avoid guys who want commitment and entanglements?

For Really Easy Ending

Dear FREE:

My best advice is always the simplest: Communicate. The same conversation in which you tell what you want to do to each other, you gauge his interest in more than sex. If you don’t match up, be willing to throw him back and fish for another catch.


Related Posts

Atlanta Pride: Ava Max to Headline the Festival

Global pop sensation Ava Max will headline the 2024 Atlanta Pride...

Pride Ball @ One Magical Weekend

Photos by Russell Bowen-Youngblood

Therapy Pool Party Sunday @ One Magical Weekend

Photos by Russell Bowen-Youngblood

Juneteenth: Honoring Freedom and Heritage in Atlanta

Edited by Mikkel Hyldebrandt Juneteenth, celebrated on June 19th, marks...

Broadway Babes: Mr. Man Shines Its Spotlight on the Year’s Male Tony Nominees

By Anthony Ruberto The 77th Annual Tony Awards take place...