Dear Dumbs,

Dear Dumbs,
You guys kick bootie. And speaking of bootie, I’m hoping for a little guidance. I’m closing in fast on my 40th birthday and as far as relationships go, you can call me a failure. 

My life is filled with failed relationships and even a failed marriage. When I examine each, it’s hard not to take responsibility for all of them going south. I love the “idea” of a committed relationship and being faithful to one man, but I’ve yet to do it. I have cheated on every guy I have ever been with.

I love the thrill of getting to know someone, and I usually fall for them when I do. The problem is that I get bored easily and then go looking for my next thrill. I don’t want to live the rest of my life as a cheater. Do you think it’s possible for me to do so? Or at my age am I a lost cause?

Shelby H.
Pensacola, Florida


TERRY: Your parents named you Shelby. You never had a chance.

SHARI: I hate to ask, but what do you mean, Terry?

TERRY: This probably isn’t the place to tell you, but I’ve had sex with 22 Shelbys.

SHARI: But who’s counting?! Anyway, Shelby, I think you’re looking at this wrong. It seems like you’re feeling pressure to be in a monogamous relationship. I’d like to be the first to tell you, it’s OK if you’re not. It’s not for everybody. I mean, think of the benefits: You wouldn’t have to put up with someone’s bad jokes, for starters.

TERRY: Good thing all my jokes are money. Shari is right. Finally. If you’re up front with all your newbies, then it’s on them to continue seeing you. But I’ve known people who have asked the same question and a lot of them are happily married now. 

SHARI: Seriously, Shelby, you don’t need to be in a committed relationship to complete you. As long as you’re honest with your romantic partners, no harm, no foul. Everyone knows what’s expected.

TERRY: There’s really two answers to your question. Shari is right. That being said, I think it’s possible you may tire of it and meet the right person who makes you feel alive. As far as your age goes, this may be the right time to keep your eyes open for that guy. Good luck!