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Ask Anna: I’m in a dating rut. Help?

Ask Anna is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.

Dear Anna,

Me: local, “out of loop” single, handsome male in hunt of a chill bar date. I beg of insight. Help me find the perfect woman please. —Anon.

Dear Anon.,

Have you tried the Container Store?

OK, OK. Here’s what you do when you’re stuck in a dating rut. Three things:

Change your behaviors

Change your outcome

Change your expectations

What do these look like in practice? Changing your behaviors means trying new approaches to how you go about meeting these “chill bar dates.” I might even go so far as to say do the exact opposite of what you’ve been doing. And see what happens. If you only meet women on Tinder, delete the app and start approaching women in person or ask to be set up by a friend. If you only meet women in bars, try the library or the ice cream parlor or the 24-hour White Castle. If you’ve been doing “nothing,” do EVERYTHING. Treat your romantic life like a science lab. Assess what works and what fails spectacularly. Make notes! Make spreadsheets. Or don’t. (Spreadsheets are fun though.) And go from there. Have a ball with your experiments. It’ll give you good stories, at the very least.

Changing your outcome means that maybe the goal itself is flawed. Your use of the words “perfect woman” is telling. There is no perfect women because all women are perfect — have you even seen Beyonce lately? God, her business acumen is so hot. OK, no. No one is perfect. I challenge you to find the most imperfect woman alive and buy her a drink. Expand your ideas of compatibility. Perhaps your perfect woman is nothing like you. Perhaps her limitations are what enable her to soar. Perhaps your chill date wants more than just a bar rendezvous. Are you open to every possibility? Doing so will increase your chances of being pleasantly surprised. “There is a crack in everything,” as Leonard Cohen sang. “That’s how the light gets in.”

Changing your expectations means only this: It’s really hard to meet people we connect with and want to spend time with and be intimate with. It can take YEARS. It can take much therapy. It can take failing 683 times and then a few more. I’m not saying “don’t try,” but I am saying that if we go into something with a very reasonable and manageable expectation, it’s harder for us to be crushed by defeat. And I don’t want you to be crushed by defeat! Progress may be slow, but don’t let it keep you from moving at all. There’s a difference between struggling and standing still. Keep trying to connect. Keep trying to improve yourself and the lives of those around you.

And one last truism, which I probably gleaned from another perfect woman (Oprah): The more we invest in lifting others up, the more people are drawn to us in return.

Good luck, Anon.

Anna Pulley is a RedEye contributor. Want to ask Anna an anonymous question about love, sex or dating? Send it below, or email redeyedating@gmail.com.

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