When Drug Dealers Break Up

Dear Dategirl,

My girlfriend is a good person, but I need to break up with her. The problem is that we’re also business partners. Our business is one that’s a little informal (please don’t tell the IRS) and slightly illegal, so there is no binding legal agreement between us. She has some health problems that aren’t life-threatening by any stretch, but worrying about that has kept me in this relationship four years longer than I wanted to be. She also relies on me for everything. If I’m out late with a client, she doesn’t even eat until I get home!

We’ve been together seven years, and I need to figure out how to break up our romantic relationship while still keeping our business one intact, if that’s what she wants. I’m assuming it is, because she literally has nothing else going on in her life. She is completely devoted to me and our business. It’s too much pressure for me. I’ve had a couple affairs over the years, and she even found out about one. But she was so destroyed that I’ve stopped. But I’m almost 40, and I want to settle down with someone I genuinely love, not just pity.

How do I do this? How do I break her heart, ruin her life, and possibly push her out of her job?

—Mr. Cut and Run

An informal business that’s also illegal? That smells like drug dealing to me, though I suppose it could be a happy-ending massage parlor or some sort of knockoff-designer-bag ring. How dangerous and exciting!

I’m no lawyer, but if your business operates outside the law and you want to dump your partner, I’d suggest shutting it down and liquidating your assets first—with an equitable distribution, naturally. This way a moment of fury doesn’t turn into years behind bars for you. It sounds like your girlfriend has little left to lose once you’re out of the picture, so I wouldn’t put it past her, even at the risk of incriminating herself.

Oh, and you should definitely talk to a lawyer before you do a thing. Once you and legal counsel have figured out the logistics, you just need to sac up and tell her how you feel. There will be tears. There might be yelling too. But the best thing you could do for her is cut her loose, because nobody wants to be anybody’s pity fuck.

Except when they do.

Because, you see, some people are completely happy handing their well-being and sense of purpose to others. Conveniently, they’re generally drawn to martyr types who are nearly pathological in their need to run the show and take care of everyone. Sound familiar? Maybe just a little?

After all, it feels good to be needed, no? Nothing wrong with that.

Until there is.

The two of you have formed a sick little alliance, and it’ll be best for you both to get out and get help instead. She needs to figure out why she’s incapable of feeding herself when there’s not a man around, and you need to get over your attraction to wounded pixies so you don’t end up in the same shitshow down the line. While you’re at it: Straighten your ass out and get a legal job. There’s nothing attractive about a 40-year-old felon.


Want more? Listen to Judy on The Mike & Judy Show, follow her tweets @HitOrMissJudy, or visit dategirl.net.

comments powered by Disqus

Friends to Follow