Miss Information

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 So he's not a) half your age, b) a jerk to the waiter, or c) a Scientologist. Great!

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Dear Miss Information,

I'm 31, and spent my early-to-mid-twenties chasing guys who definitely weren't interested or who lived in far off places, so I've really only been traditionally dating for a couple of years. I have yet to have a long-term relationship. I've finally worked through a lot of my issues and am ready let my guard down and open up. The problem I'm having is that once I like someone and it feels like things are at the point where it will either progress into relationship territory or not (usually 2 months-ish in), I get really anxious about where it's going.

Because I've never really made it past that point, I'm always looking for signs that things are winding down, reading way too much into small things and over-reacting, which takes a lot of emotional energy and gets in the way of my getting to know that person further. Sometimes I even end things (or at least think about it a lot) just to cut to the chase, instead of letting things play out naturally in their own time. How do I keep my anxiety in check? And how do I determine when it's not just my anxiety kicking in, but there are some actual signs that it's not working or not a good fit?

—Anxious in Dating

Dear Anxious in Dating:

Good news! This problem is universal, and has nothing to do with your perceived inexperience. 

Bad news, though! This problem is universal. Even if you get married and mean "til death do us part" literally, you will still have rough patches where you wonder if the union will make it, where it is headed, or whether that IHOP waitress really meant it when she offered the threesome.

Of course, knowing you are completely normal is no consolation when the banshees in your head start telling you to run. So how do you separate legitimate concerns from illegitimate panic? The answer, like most solid advice, is tedious and unsexy. "Practice."

This is really an issue of trusting your inner compass; finding a solid dude is merely a fringe benefit. Start by writing down a list of non-negotiables. These should be things you hold dear, absolute deal-breakers. Keep this list concise—5-10 things, max—and even post it near a desk or a dresser if you're afraid you'll forget. When you find yourself questioning your date, ask yourself: "Is this one of my non-negotiables?" If so, you're allowed to close your bar tab and go home early. If it's not, withhold judgment and keep feeling it out. 

The gray area annoyances are much harder to read. So he's not a) half your age, b) a jerk to the waiter, or c) a Scientologist. Great, he passes your core values! But if you're still not feeling it, think through—or write down—the things that bug you, then judge how real those things are. Can you look past the fact that he misused the word literally? Probably. Should you look past the fact that he slandered each of his exes while you stared at your Spaghetti Carbonara? Probably not. Also, pay special attention to any time you use the word "but" when you describe him: "he's really dumb but he's hot," or "he collects guns and knives, but he paid for dinner." "But" often signals that you're settling.

If you really aren't sure of your instincts yet, take things slow until you can trust that you have a keeper on your hands. Also, know that you will occasionally fuck up; we all invest in the wrong people at one point or another. Good news: most of us struggle with this! Bad news: Good luck, because most of us struggle with this.