Dating Disasters—Solved!

Stop suffering through these courtship nightmares. Get any date back on track smoothly with our clever tactics.

By Alix Bookbinder

ou’re really into your new sweetie: that contagious laugh, that curly hair, the way this person really gets you. But soon, little issues twist into bigger problems that you suspect might spell the end of a budding relationship. Before you throw in the towel, break out one of our solutions.

The dating drama: He's always leaving his wallet at home
The fix: If it happens once and he seems genuine, you can always offer to pay—in fact, you may have no choice. Your next move depends on whether he insists after dinner on going back home to get his wallet or if he apologizes when he asks you out again: those are signs he may just be scatterbrained. But if he’s got too elaborate an excuse for why
Even a guy who’s lost his wallet will usually just borrow some money from a friend rather than mooch off a date.
he’s cashless, consider yourself warned: Even a guy who’s lost his wallet will usually just borrow some money from a friend rather than mooch off a date. And if it happens twice? A guy who never offers to pay (forget “forgets”) isn’t in it to win it—move on. “On early dates, people will tell you through their behavior who they really are,” says romance coach Kathryn Lord, author of Find a Sweetheart Soon! Your Love Trip Planner for Women. A cheapskate isn’t investing anything—heart or dollars—in you.

The dating drama: He always just wants to stay in, but you think it's boring
The fix: Who doesn’t love snuggling on the couch with her sweetie, sharing a pint of Dulce de Leche? But when even a “romantic dinner” means “Let’s go get some pizza and split a pitcher,” women can feel the romance slipping away. “Relationships are not made either his way or your way,” cautions Lord. “They’re a third way you build together.” She recommends taking turns planning dates. His might be an all-Sopranos evening at home, but you get to choose something as romantic as you want when it’s your turn—and seeing you happy should be enough of a payoff that your guy won’t mind a night out. Of course, you can always suggest an activity guaranteed to fascinate any man (no, not a strip club): Relive your adolescence at an arcade, try a Korean BBQ joint with a tabletop grill, or challenge him to some pool or darts at a local bar.

The dating drama: He keeps you waiting forever, every time
The fix: Onika from Brooklyn’s boyfriend has a common problem: chronic lateness. “After fifteen minutes, I’m so grumpy that when he finally arrives, it’s not even worth it.” What to do, then? “Take a step back,” suggests Lord. “If there’s a power struggle from the beginning, it doesn’t bode well.” When a guy leaves you waiting, he’s telling you that his time is more important than yours. First, calm down and cut him some slack—some people will just never be on time, so just plan to show up 10 minutes after the scheduled time. Second, tell him that’s he’s got a 15-minute grace period: If he doesn’t show up by then and hasn’t called to let you know why, you’ll assume he’s standing you up and leave. Now, this is the tougher part: follow through with it. After just one cancelled date, he’ll realize that if he wants to continue dating someone as busy and fabulous as you, he’ll have to respect the plans he has with you. The end! (This applies to us ladies, too. It’s not cute to always make a guy wait for you to get gorgeous!)

Alix Bookbinder is a writer in Brooklyn whose work has appeared in Bust, Philadelphia Magazine, and other publications.
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