I'm exactly 40 years old and have started seriously dating again for the first time in 8+ years. Go me, I'm proud of myself for doing this! I'm going on a date tomorrow for the first time in over a year. Since I've started dating, I keep running into an issue... I have 2 DUIs in my past. Now, because I'm so good at my job (HS teacher, helping to keep future generations positive) and have such a fabulous family support system, the only consequences I've suffered have been financial. I'm one of the most "stable" dudes on Grindr, even if I only make five figures. So when and how is it appropriate to tell a potential partner about my past legal troubles? (There are other issues, too: not being able to bottom without poppers; not being able to top, period... but those I can work through with my shrink.)

Although there are more issues, which you shouldn't have to deal with, the crux is this: when and how do I say "I have 2 DUIs, and I haven't given up alcohol, but I never, ever have a drink when I have to drive and I never, ever will?" And, in the last 10 years, that has become obsessively true: if there's even a chance I get behind a wheel, I abstain for 24+ hours.

Disclosing Unfortunate Information

Frankly, DUI, I think the must-have-poppers and no-can-top issues are likely to be bigger problems for you than those two DUIs in your rearview mirror. You still have your license, it seems, so it's not like you'll be asking your dates to do all the driving on top of all the fucking, right?

Zooming out...

No one gets to 40 without baggage. Sensitive, sane, smart guys—the kind of guys you'll wanna date—score people on generous curves, curves that allow for some past screw ups. So long as lessons were learned and those particular screw ups are not going to be repeated, a relatively common-if-serious-and-always-regrettable legal issue is likely to be taken in stride. Of course a DUI might be an absolute dealbreaker for some guys (guys who've lost relatives to drunk drivers, for instance, or guys who have vacation homes in Canada). But since you can't control how guys are going react to the news you'll need to calm down about it and be strategic about it.

It's up to you to decide when or whether to disclose your driving record to a new guy. But when you order your first round with Mr. Promising New Guy You Met On Grindr, DUI, there's no need to blurt out, "Hey, on the subject of booze, I want you to know I have two DUIs and I won't be driving myself home tonight so bottoms up!" Because that would be equal parts odd and unnecessary, and consequently a total buzzkill. Because in addition to telling him a potentially off-putting fact about your driving record, DUI, you would be telling him some definitely off-putting things about your judgement. ("I have no common sense, crappy interpersonal skills, and poor impulse control!")

Bring up the DUIs when you have to, need to, or you reach the point where sensible people who might be getting serious about each other start to disclose their baggage—a point that typically comes right before or shortly after you start introducing each other to friends as your "boyfriend." By that point, DUI, he'll have seen you drink responsibly. He'll know you're the sort of person who would never get behind the wheel of a car impaired because he seen you impair yourself a few times and then Uber your ass home. He'll be better able to weigh the person he knows you to be now against a fact about you from your past.

And when you bring up your DUIs, DUI, keep it simple, be honest, and be direct. Don't be dramatic, don't apologize endlessly, don't beat yourself up—and don't be flippant either. Talk about your experience, let your new boyfriend react how he will, and then continue sharing all the other great and awful things about yourself.