Cupid is not OK: 5 ways to fail at dating

Tinder fail. Match fail. IRL fail. See how you too can fail at dating me.

Jessica Ridpath
Jul 15, 2016 · 4 min read

I am a single, 41-year-old heterosexual female. I have three kids and a good job. If two-thirds of that didn’t already scare you off, then you’re one of the few. You may read on.

I’m a smart gal. I like a good joke. I have been told I’m attractive. More than once. But in the nearly four years that I’ve been single, the dating fails have stacked up like Seattle rush-hour traffic. Only less satisfying.

We’re in this together. The problem with dating is that when one party gets an F, it’s a failure on both sides. But try, we must. Learn, we must. So in the interest of social science, I present you with five surefire ways to fail at dating.

Don’t do any of the following:

1. Tap into your inner frat boy

Show up to your first date wearing a baseball cap. As your date gets up to greet you, flop yourself down in the booth across from her. Kick your feet up on the bench. Stare down at your menu as you make initial small talk. When you finally look up at your date, say “Mmm, mac ’n’ cheese.” When the waitress comes, order mac ’n’ cheese. Show your date pictures of your recent trip to Comic-Con and describe your favorite video games. In detail.

2. Be totally different on the second date than you were on the first

On the first date, be a good conversationalist and share funny, interesting stories about your life. Listen and laugh as your date shares funny, interesting stories about her life. Be attentive and engaging, and say good things about your family and your job. Smell nice.

On the second date, forget everything you talked about on the first date. Ask your date all the same questions you asked before. Interrupt her often as she tries to answer you. Lose your train of thought mid-sentence at least three times. Talk about how you hate your job and going to your kid’s baseball games. Smell like you took a bath in perfumy fabric softener.

3. Talk about everything but yourself

Over the course of several dates, talk about everything from travel to politics to sports. Describe what’s going on with your job, your house remodel, and your next backpacking trip. Keep it up until you completely derail.

When asked what you like most about your job, say “I don’t really know.” When asked what drew you to this part of the country, say “I’m not sure.” When asked where you’d most like to travel, say “That’s a tough call.” When asked if you and your siblings were close as kids, say “I can’t remember. I wish my mom were still alive so I could ask her.” Change the subject after each non-response.

4. Talk about nothing but yourself

First, be tall, fit, and breathtakingly handsome. Next, be intelligent, articulate, witty, and successful. Finally — and this is the most important part — know that you are all of these things and be openly proud of it. Use these assets as a free pass to shower yourself with praise throughout your first encounter with your date. She will be too busy gazing at your biceps to notice.

Talk about how your divorce was pretty much all your ex-wife’s fault and how you’re definitely the better parent. Your date will be too distracted by your charismatic smile to judge your words harshly. Explain how you started a business that has become so successful that you hardly have to work anymore. Your date will be too impressed to care that you’re bragging.

In fact, your date won’t catch on to what a conceited prick you are until you cancel your second date by text message. Make yourself feel better about being a conceited prick by using the classic “it’s not you, it’s me” refrain. If you’re feeling especially creative, try channeling Gwyneth Paltrow and crafting some flowery language like “I just can’t fight this undeniable intuition that we don’t complement each other on that deepest of levels.” Pat yourself on the back.

5. Ask for snacks

Be several years younger than your date. Help her get over her qualms about dating a younger man by being kind, respectful, and talented. Being hot and great in bed will help, too. Laugh together as she makes tater tots and frozen corndogs at midnight after the first time you sleep together. Make a joke about how great it is to date a single mom because, you know, snacks! Then take her back to bed so she’ll (hopefully) forget that you said that.

This last bit is the tricky part. You have to get the timing just right. The next time you arrive at your lady’s house for a sleepover, wrap her up in a big hug, and then say, “Can I have some snacks?”

Congratulations! You now know how to avoid five proven dating fails. Please direct all questions and letters of thanks to the nearest mountaintop convent, where I’ll be working on my next article, “5 ways to cope with being celibate.”

© Jessica Ridpath

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The Hit Job

humor | culture | football | trouble

Jessica Ridpath

Written by

Jessica is a writer, chauffeur, sock wrangler, and senior research communications consultant at Kaiser Permanente Washington Health Research Institute.

The Hit Job

humor | culture | football | trouble

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