Miss Information

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Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

I’m shy when it comes to approaching women. Where does a single guy in his twenties meet someone? I have many girlfriends, but they don’t seem to be keen on hooking a brotha up with their friends. Internet dating has been a total miss, and bars are not my scene. Some women I meet via social and political concerns are pretty awesome, but who wants to ask someone out in the middle of a community mental-health symposium? I’m at a loss. Are there other cool guys out there wondering the same thing? — Perpetually Single


Dear Perpetually Single,
Everything you’re doing sounds well adjusted. Why not try doing some stuff that’s not?
Plan A
Get a chihuahua. A teacup chihuahua. Dress it in a hoodie or a satin jacket and take it for walks at the park. Now, I know that dog ownership is a big responsibility, but if you do what I say, you won’t have to worry about it, because you’ll have a new girlfriend within seventy-two hours. She can help with the pooper scooper and will be more than happy to play dog mommy.
Plan B
Go to the sheet aisle of Linens-N-Things. Walk around looking puzzled and ask a cute girl to help you choose a thread count. It might sound weird, but bed linens are one of those things people feel very strongly about. Either they don’t care, or they’d rather have invasive surgery than watch someone buy inferior sheets. You’ll know you’ve got a winner if she starts blinking furiously and her eyes go all crazy big. This ploy also works well in the kitchen implement section. You can quiz hotties about pretty much any item except the nutcracker and the turkey baster, for obvious reasons.
Plan C
There is no Plan C.
My best advice for you, Perpetually Single, is to get bolder about asking women out. You say you can’t ask a woman out at a conference, but why not? I’ve been to those events and I’d die for an excuse to get away from the Radisson Executive Lounge. People are like caged tigers in there. You also need to try Internet dating again. Find someone who’s skilled and shadow him. Solicit harsher-than-harsh profile advice from your female friends.

Dear Miss Information,

How do women feel about dating guys who don’t have any friends? I’m single, in my early thirties and new to the area. All the guys I meet are married or they’re not people I like enough to be friends with. Actually, I’m not even that interested in making friends. I don’t have the time or motivation and I’m happy on my own. What should I do to make this not look weird? — Mano Mono

Dear Mano Mono,

When I go on a date with a guy who’s a lone wolf, here are my worries: 1. He’ll be overly attached and clingy; 2. He’ll be a big time suck and I won’t get to see my friends. After he’s charmed me with numerous compliments and free refills of Diet Coke, I start looking at what’s good about it: 1. We can go out and I don’t have to be "on" all the time in front of his buddies, 2. He has more time to devote to me than my see-you-once-a-week ex.
You can reassure your dates that you’re not keeping a torso in the cupboard by occasionally namedropping "pseudo-friends" like your coworkers and hometown friends. They don’t have to know that the "Roy" you’re talking about lives really far away and that "Bob" is a douchebag colleague you can’t stand. First, second and third dates don’t require this kind of raw honesty.
Finally, don’t put so much stock in it. There are a lot of people (including dateable women) who have very few friends. If you act like it doesn’t bother you, it won’t bother them. Most girls would rather be with a guy who’s had some interesting experiences and can cope with change over a guy who never leaves town and has a hundred people at his birthday party.

Dear Miss Information,

I was talking to a thirty-year-old woman who had been dating a man twenty years older. She said he was the kindest, most generous man she had ever met and she liked him a lot. But her lady friends harassed her so much about dating an older man that she couldn’t take it anymore and broke up with him. Why do women find it so disgusting for a woman to date an older man? Women in almost every other country think older men are a great catch. — Old Guy Wondering

Dear Old Guy Wondering,
The older man/younger woman dynamic pisses women off because it reinforces the stereotype that, when given a choice, women would rather date a guy with grey pubes than a young, sexually viable male. It’s a stereotype bolstered by decades of media brainwashing and an assortment of bullshit myths.
Bullshit Myth #1: Women want an older man because they need his money.
We have jobs. We might not have great dental, but we do okay. A good number of us out-earn our boyfriends. The fact that you take home a little more scratch than a male in our demographic does not soak our panties.
Bullshit Myth #2: Women want an older man because they want a husband.
Not all of us. If we do, what makes an unattached guy of an advanced age such an attractive romantic prospect? Is he so unpleasant that no one wants him? A playboy? A bitter divorcé? Thanks, but we’d rather look elsewhere.
Bullshit Myth #3: Women want an older man because they don’t care about looks.
Fuck that. Says who? Does having a vagina mean you’re visually impaired? Attraction is important and we’re going to gravitate toward whoever’s hotter. Granted, there are some great-looking older gentlemen out there, but this usually means younger men.
Bullshit Myth #4: Women want an older man because they aren’t that into sex.
Of course we’d rather cuddle with your floppy, temperamental boner than be fucked senseless by a guy in his twenties. A man so experienced and debonair makes it all worth it. You keep telling yourself that and we’ll keep pretending we believe it.
Okay, now that I’ve completely alienated half of my readership, I should say that I have much love for older men. Read this as a riff on lame cultural beliefs rather than a sincere personal attack. Seriously. I also know for a fact that a lot of you ladies actually prefer gentlemen of a certain age. What are your reasons? Share them in the Feedback section.


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