Dear Tits and Sass,

I’m 28 and I’ve been a stripper for almost seven years. The last couple have definitely been the hardest, but the most profitable. I’ve created a life better than I could have imagined for myself before I started dancing—riding horses at nationally rated jumping shows, buying a house, driving a nice car, zero student debt and actual time to go to college as an adult, traveling to marathons and going on luxury vacations often, eating healthy food, and more. I wake up every day to a life I love, good friends, my pups. I’ve spent the single years doing my own thing.

I’m ready for and really want a partner. I haven’t dated in almost five years, save for a month of dating an impotent obese man. My 65-year-old customers probably have exponentially more sex than I do. Dear God, I want a steady flow of conversation that doesn’t involve being paid, and holy cow I would love a steady supply of dick before my vagina dries out like the Sahara. Online dating was a big fail on one free site and two paid sites—the few dates I had were either okay and didn’t work out, or sucked. I choose not to date customers of the club I work for as a personal boundary. I’m not so much into casual sex, but the few partners I’ve tried have led me to believe that I’m an unsatisfying-penis magnet.

It’s gotten to the point where even thinking about dating really sucks, and makes me unhappy for days when someone brings up the idea. It seems like as soon as I reveal my job, guys either flee or do the “trophying” thing until it quickly gets old for them. Recently, a friend wanted to introduce me to her boyfriend’s attractive pal. When I asked her if she’d told him about my job, she said she and her boyfriend would wait for me to tell him.

I feel like I’m tricking someone into a date with me if I don’t come with a huge red flag, a scarlet “S,” and some infamous Jaws-esque warning music. I don’t want to quit my job, and I’m not apologetic about what I do, but it does seem to be a big deal to men who aren’t meth addicts, have all their teeth, and live indoors. I don’t think it’s fair if they’re set up on an outing with me if they’re being…um, tricked. I’d want to know if someone was setting me up with someone that had a pretty big possible dealbreaker.

My question is: How in the fuck do I start dating again? Do I tell prospective gentlemen about my job, and when? Should my friend tell this man about my job before he decides whether he would like an outing with me? Do I lie entirely for as long as I can, despite my work being at obvious hours, and the stilettos and g-string laundry that litter my house? How long do I lie? Do I really have to wait another six-to-sever years (quittin’ time) before men will take me seriously as a partner?

Sincerely,
Calloused Masturbation Hand