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My First 20 Dates

My First 20 Dates


Is dating difficult? It had been over a year since I'd gone out on a date, and wasn't completely certain I remembered how it all worked. Leaving fear aside and with a healthy lust for adventure, I decided to go on 30 dates in 30 days. That would be a surefire way to reeducate myself in the designs and strategy of "how we date." I'm two thirds of the way through and have definitely learned a few significant lessons.

Don't take yourself too seriously! No one else is. Unless you're Justin Bieber or the secretary-general of the U.N. (wouldn't it be interesting to see them go out on a date), then chances are you're just a cool guy looking for another cool guy, and all of us have something special hidden up our sleeve. Sometimes it's the simple mundane facts of your life that interest potential partners more than knowing how to speak Klingon and five other sci-fi languages.

Wear comfortable clothing. The last thing you want is to be attempting to impress in the tightest outfit known to mankind only to find out that your date has planned a picnic at the top of a nearby mountain. That shirt that looked so nice in the club the other day may not be so jazzy covered in burrs, sweat, and tears.

Silence is within your control. Despite what people assume, silence does not just happen. It's the carefully orchestrated outcome of disinterested or bored parties. There is always something to talk about, and even if your date is going to ultimately crash and burn, give the airplane controls a few extra tries before pulling the ejector seat handle.

Listen. I always feel that rush of excitement when my date makes a funny joke remembering something topical I had mentioned hours before.

Don't forget to eat. I'm a complete bitch if I don't get food on a regular basis, and there's nothing wrong with suggesting an amuse-bouche even if it alters the plans of your date. Better to be lively and on target than hypoglycemic and annoying.

Don't have a glass of wine every 30 minutes. Eventually your date will devolve into a comedy of errors, and the person you want to be on your date quickly becomes Patsy Stone.

If you want to discuss sex, do it in a playful way. There's nothing wrong with inquiring about an activity that, if you've gotten this far on the date, is likely to occur. However, if the date turns into an interview for Hot Times Quarterly, you could easily turn your date off.

There are no taboos anymore. I've heard countless times about how you're not allowed to discuss ex-boyfriends, religion, politics, sex, death, money, or constitutional law on a first date. I don't buy into any of that. If it feels like a topic worth exploring, then do it. Respect your date's boundaries, but don't live inside a conversational prison camp.

Friends are allowed. Some of the best dates on this adventure involved hanging out with my potential mate's close friends. You can learn a lot about who a person is by seeing his confidants and watching how they interact. Plus, if things go well, hopefully they're going to be your friends too. If you hate all your date's friends but love your date, there could be something wrong there.

Beware of dates in cemeteries. This one is self-explanatory.

Movies are not evil. Yes, there's not a lot of time to get to know a new person sitting in a movie theater, unless you're Chatty Cathy or Frisky Francesca. But I for one love the post-movie analysis with someone I'm trying to get to know. I really enjoy the cinema, and if your date does too, then go for it.

Leave your comfort zone. If your date wants to go shoot a shotgun at a firing range and you've never picked up a weapon in your life, just take a deep breath and ask yourself what's the worst that can happen? Dick Cheney shooting that man in the face was a total aberration, and it's unlikely to happen on your first date.

Farting happens. Burping also happens. Don't lie about bodily functions.

If your date is not making fun of you, yet then preempt him and make fun of yourself. I think it's endearing when a date delivers a little self-deprecating humor, and God knows I've been making fun of myself since October 1. I'd rather be making someone laugh than wondering if he's laughing at me.

You're not nervous. You think you are, but you're not. If your date is the cover of Men's Fitness magazine and you're certain he doesn't like you, well, then I guess there's nothing to be nervous about, is there? Just be yourself and enjoy the day. You can tell your friends about it later after he ends up asking you on a second date.

Disregard any and all things I've said if you don't agree with them. If you're willing to take advice and you think it'll work, then I'm happy my adventure has helped you out. If you think I'm blowing smoke up everyone's caboose, then it's more important to trust your gut and be yourself.
Advocate Channel - The Pride StoreOut / Advocate Magazine - Fellow Travelers & Jamie Lee Curtis

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Kevin Richberg