I’m going on a date this weekend. (My hundredth.) I always get my hopes up, and usually find them smashed like a Halloween pumpkin. So what do I do? Start expecting the worst so I’ll be pleasantly surprised? Or look forward to them and be disappointed? —Erin

Great, great, great question, Erin. When I used to get ready for dates, I’d flip-flop back and forth between high hopes and low expectations every run of the flat-iron. With that experience and what I’ve learned, here’s what I think: Have high hopes for your future love life—that you will find the love of your life—and remember that this date is part of the path that will get you there.

Maybe he seems like he could be the guy! Or maybe he’s so totally not even similar to a choppy faxed version of the guy that you want to go home and eat a whole pizza by yourself. But either way, this guy—this date—is one step closer to the one you’re meant to be with. The world is putting you in front of him for a reason: Maybe to learn something from him. Maybe to learn something about yourself. Maybe to see how hilariously terrible dating can be sometimes, so that when you do meet your big love, you won’t miss your single days quite as much.

So that’s what I think. Don’t expect the worst. Look forward to what you can learn from your hundredth date. And toast with a glass of something that you still have two important things after date ninety-nine: perseverance and humor. The right guy will find that so very charming.

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