Filed Under: Christopher Stetson Wilson, Online Dating Tips, Valentine's Day

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Happy Valentine’s Day! Or, if you’re anything like us: sad, lonely Valentine’s Day. The exception here at MCD is resident ladies’ man Christopher S. Wilson, who yesterday explained how to attract women in an online dating profile with dignity and class (mostly by not referring to yourself as a ladies’ man). Today, in part 2, he guides you into foreign territory by actually writing to (*gasp*) a real woman.

SEND A GREAT MESSAGE

Chances are good that you have nothing useful, entertaining, or even microscopically interesting to say to women, or to anyone who has lived, or ever will live. The messages you send out should do four things:

1. Stand out.
2. Start a conversation.
3. Not scare the %$&! out of her.
4. Not sound like it was written by a cat walking on your keyboard.

The following messages violate one or more of these rules:

• hi
• 
• How are you? I really liked your profile.
• I was browsing around and saw your profile and you seem really interesting to me so I thought I’d say hi and see if you’d like to chat because I think we’d really get along well.
• I know you are thirty years younger than me but you are the most beautiful girl I have ever seen. If I can’t have you I will be forced to turn to a life of pony abuse.
• sup gurl. r u dtf?

BE DISCRIMINATING

Just because you have a penis and she has a vagina does not mean you are a perfect match. Read the profiles and heed her requirements. If she says “No barber,s” don’t write her explaining if only she’d give you a chance she’d see how great barbers are. If she says “I’m sorry but I will not date you if you are overweight,” either find someone else or hit the gym. Women learn, through trial and error, just as you should, what they like and don’t like. It is not your place to show them the error of their largely rational prejudices.

DON’T ASK OTHER STUPID QUESTIONS

If you can look it up on the internet yourself, don’t ask her to explain it.

DON’T ASK STUPID QUESTIONS

“How was your weekend?” doesn’t work. Nor does “How’s it going?” It’s not specific to her and brother, is it boring.

DON’T ASK ADDITIONAL STUPID QUESTIONS

I know you’ve been taught to fake an interest in other people, since they’ll like you more if you show an interest in them. While this principle can be valid when you’re actually interested, it’s not valid when you’re just manipulating the device to get them to talk to you. It’s hollow and pathetic and women see right through it. This leads me straight to the next point:

START A CONVERSATION NORMALLY

She’s not a goddess. She’s not perfect. She does not want to have sex with you. She’s a random person you happened upon who didn’t invite you to even talk to her. But just like a girl you meet at a party, she’s probably at least marginally interested in talking to SOMEONE. So address her like you would anyone else you meet randomly, man or woman. Tell a joke, make an observation, share a weird anecdote. Your profile already represents you. The message is a chance to get her attention, but give her a chance to reply within the context of a conversation two people might actually have in public.

DON’T PILE ON THE FLATTERY

Compliments are usually appreciated, in particular if you compliment something unusual they don’t usually hear. But leave out the crap about how they have the most amazing eyes. Don’t tell them they’re hot or beautiful. Just have a conversation about stuff.

Christopher S. Wilson

DON’T POINT OUT THE STUPID CRAP YOU HAVE IN COMMON

And don’t point out how you meet her list of requirements. She can read (hopefully). Just because you have a beard and love Law and Order: SVU marathons does not make you a couple. It doesn’t mean she will like you. It just means that perhaps you will have something to do on a second or third date. That’s all.

DON’T BE A JERK

The pick-up artist community (yes, such a thing exists) famously refers to a technique known as “negging”. That is, being critical or in some way negative toward the girl instead of dumping flattery on her. It could be as simple as correcting a spelling error (“You misspelled ‘disfigurement’”) to pointing out flawed logic (“I’m concerned about the strong multicollinearic relations between the variables in your chi-squared distribution”). Being bratty demonstrates a degree of self-confidence in the right context. But this is the wrong context. Unless you really know what you’re doing, you’re just going to come across as a jerk. Don’t call her names. Don’t tell her she’s crazy or has psychological problems. And for the love of God don’t call her fat. It’s not only counterproductive, it’s ANTI-WOMAN, and she will not respond. If you’re not sure if what you want to say is mean, then just don’t say it at all. If you wouldn’t say it through a smile to a stranger in real life, it is probably an insult.

IF SHE DOESN’T WRITE BACK, LEAVE HER ALONE

You’re not going to talk your way into anything with an unwilling participant. If you haven’t heard from her in two or three days, don’t send a second message. She saw your first one and wasn’t into it. Walk away, save time, and stop acting like a stalker. It’s people like you that make women so scared of dating online in the first place.

STOP MESSAGING TEENAGERS

Some young women do date much older men, but most do not. The ones that do will either make their preference plainly obvious or will pursue you themselves. If you’re 48 and bald with a gut, that pale, skinny 19-year-old with the two-tone hair is going to turn to stone by the very sight of you. Message the women who will put up with your flabbiness.

EXPERIMENT

Try writing messages that are irreverent, sacrilegious, and strange, and see what happens. Send a message that is a complete non-sequitor. You may be surprised at how many women will respond to these sorts of messages, if only because they stand out from the hundreds of boring messages they get every week. Most importantly, you will LEARN something. That’s why it’s an experiment.

Christopher Stetson Wilson is a word artist and songwriter in Cambridge, MA. His many works can be found at OutsideOutside.com.