A Dating Update – Does the Gentleman or the Bad Boy Get the Date?

This is kind of a weird post for today because, to be honest, there isn’t really an update to my dating life! Or if there was it would be this: Threat Level Orange. What’s it called when you get rejected multiple times in a row? That’s what’s been happening since Christmas, whether it’s a woman I met in “real life” or an online connection. In fact, one woman even cancelled a date while I was on the way to the date! That’s certainly one I won’t forget anytime soon. Another woman cancelled twice with flimsy excuses.


I feel like the Buffalo Bills in the 1990s. All dressed up and nowhere to go. Well, they DID make it to the Super Bowl a handful of times but everyone remembers they couldn’t ever win the big game in that era. At least they made it to the championship, though, right? My dating life is actually worse. I can’t even get a single game scheduled.

Any advice on what I might be doing wrong or, ladies out there– what’s a surefire way for a guy to secure a date in 2025? I’m starting to believe being a gentleman doesn’t work anymore and, to be honest, trying to be the bad boy has worked either. I’m pretty much out of ideas.


-Out of the Wilderness


Discover more from Out of the Wilderness

Subscribe to get the latest posts sent to your email.

Published by Ben Wilder

Since 2005, I've called Nashville home. I'm the leader of the pack, which includes a 13-year-old beagle and an 11-year-old blue heeler mix. My days include writing, video editing, and other fun activities. Thanks for checking out my blog, I hope you enjoy it!

Leave a comment

Discover more from Out of the Wilderness

Subscribe now to keep reading and get access to the full archive.

Continue reading