When Good Dates Go Bad

Forgotten wallets, dark secrets revealed -- here’s what to do if dating disaster happens to you.


by Kate Wood


Cashless Creep

“We went to a bar for drinks and wound up ordering a few rounds plus appetizers. I was having a totally great time until the bill came—and he says, ‘Oops, I don’t have any cash on me.’ Look, I’m all for going dutch, but I wasn’t about to pay his way! After a few totally awkward minutes, I finally forked over the dough. When we split up, he said not to worry, that he’d pay me back the next time we went out. Figures…we never saw each other again.” —Lisa, 26

The Remedy: It’s the oldest trick in the book, but some guys still feel compelled to pull the old “forgot my wallet” routine. “Beware,” says Dr. Gilda Carle, relationship expert and author of Don’t Bet on the Prince! How to Have the Man You Want by Betting on Yourself. “If he’s cheap with money, he’s going to be cheap with love!” No matter how much you have in your wallet, say, “Oh, I have a little cash but not enough to cover the whole bill. I’ll walk you to an ATM though [over there, across the street, on the corner].” If he claims he doesn’t have his bank card, either (or it’s the proverbial lost wallet), you don’t have too many options—just fork it over.

Fully Loaded

“We went on a couple of daytime dates that were great, but then for the third one we went to a bar. We enjoyed a couple of drinks, but she wound up getting seriously wasted. I had to share a cab with her back to her apartment just to make sure she got there okay. Once we got there, she couldn’t find her keys so I had to wait with her ’til her roommate got home!” —Charlie, 24

The Remedy: On the first date, disgustingly drunk can be a deal-breaker. After a couple of great dates, however, it might just be a slipup. Try to slow down her pace with water. When she suggests another round, turn it down and say something like, “I’m so thirsty,” and get two glasses of water. Did it get ugly before you realized what happened? You don’t want to be responsible for a stranger, but making sure she gets home safe is the right thing to do. “When somebody’s drunk, they’re not emotionally available, so you have to think, why’d he put himself (and you) in that position?” Dr. Carle says. If she’s polite, contrite, and a bit bashful about her drunken antics the next day, give her the benefit of the doubt. Just make sure your next date’s for brunch, minus the mimosas.

Total TMI

“I was on a first date with this guy, and it turned out we’d grown up near each other. I asked him something—I don’t even remember what—and somehow it launched him into this long, gut-wrenching monologue about his childhood, from his weirdo neighbor to an almost-tearful remembrance of his dog. Then he started going into all these medical problems family members had had. I didn’t know how to make it stop!” —Melissa, 33

The Remedy: Lots of women long for a man who’ll open up to them—but not this much! Even if you really feel like you’re connecting with someone, there’s a limit to how much you should really be telling him or her on the first date. As soon as he veers into TMI (Too Much Information) territory, try to steer the convo back on course. For example, if he starts in on a raunchy anecdote about a trip to Tijuana, say something like, “Mmm, I love Mexican food.” Hopefully, he’ll move on to fajitas (and away from the senoritas), but if not, Dr. Carle says, make a joke. “Say something like, ‘Whoa, let’s not get into the whole open book yet.’ If he doesn’t pick up on it, then you’ll just get to know him a lot more quickly—and decide whether to pursue him further from there.”

The Ex Files

“My date suggested we meet at a small cafe near her place. At first, it was great—super romantic—and then her ex walked in. He was totally polite, just smiled at her once and went on with his evening, but she freaked out. She kept looking at him the entire meal, and even after he left, she wouldn’t shut up about him. Turns out the great cafe was their neighborhood fave!” —Eric, 29

The Remedy: While there’s no way you can get ex insurance, try to pick a place neither of you have ever been before to avoid conjuring up any smoldering memories. If an old flame (yours or hers) does happen to show up, be diplomatic about it. Say hello, or at least smile at the person, then let it go. Resist the temptation to dredge up the dirt, and instead, ask about her job/dog/car -- anything but her ex. “If she’s not letting it go, tell her that you’d love to see her again, but you want some time to go by first so she can get over her ex,” Dr. Carle explains. “And if she can’t handle it, add yourself to the list of men she once dated.”

Rules of Distraction

“This guy and I had just sat down at a bar when a friend of his from grad school spotted him. The two started talking (seriously boring engineering stuff), and pretty soon I was ready to put my head down on the table and go to sleep! Finally I made my excuses and left—while they kept right on talking!” —Beth, 32

The Remedy: Instead of simply smiling and then biding your time, use this as a great opportunity to do a little research. As soon as you and the friend are introduced, lead off with something like, “So how did you two meet each other?” Before you know it, you’re on to something (e.g., “Oh, I didn’t know you went to school there,” or “I love that neighborhood! How long did you guys live down there?”). If you find that they’re getting really long-winded, change their course entirely (“So there’s this really great restaurant I’ve been meaning to try”). But if he’s more interested in being with his buddy, “Let him!” Dr. Carle says. “Read the sign for what it is and move on.”

Remember, everyone's sure to hit a few relationship road bumps (though those first few dates can be especially treacherous). Use your judgment to decide whether you think this is an isolated incident or a preview of things to come, then decide what your next move will be. After all, even the lamest mistake can be an opportunity for an amazing, seals-the-deal apology.