Pick Up Women Online Without Being a Creeper

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Dear Anna,

I follow you, not in a creepy way, but online. I frequently read your blog and was wondering if you could share with me a few tips. Have weird middle-aged men ruined it for all of us, or is there something a normal but busy gentleman such as myself just looking to meet friends -- or, god forbid, get a date -- could do?

Ineeda Date

As far as I know, middle-aged men haven't permanently ruined anything, except for my Thursday karaoke nights at TGI Friday's. Jimmy Buffett himself couldn't compete with those Hawaiian shirt-clad crooners! (I think that's the grossest thing I've ever written.) It's true that lots o' ladies are wary of strange men on the Internet (and in life), but we are usually capable of discerning the trolls from the troubadours, if you'll continue with me on this karaoke metaphor a little farther. How do you make sure you fall into the later camp? Here are a few guidelines, based on common sense, experience, and a brief sampling of gals I play croquet with (I wish that were a euphemism).

Compliments

If you're going to compliment a woman, don't go immediately for her physical appearance. Yes, we like the validation, and you can be damn sure we're objectifying you too, but for the first few exchanges, choose wits over tits. I was recently charmed by, and went on a few dates with, a gentleman who wrote to me on Facebook that he was a fan of this column. Compliment her on the work she does, her insightful comments on string cheese, her hobbies, and so on. And please make it sincere. If her poetry reads like something a sexually precocious third grader would write, then don't lie about how Proustian her rhyming couplets are. 

Twitter and Facebook pro Carie adds: "RT something the girl tweeted that was clever/impressive; add a short remark of agreement. Don't be overflattering or obviously fawning. Even a simple 'true dat' is a good first step. Also, you can reply insightfully to a comment she wrote while still on-topic for the thread she was commenting on. In other words ... show your smarts but don't show off."

Not IMpressed

Don't start your correspondence with an IM (instant message), whether on Gchat or Facebook chat or an online dating service IM window. It's intrusive and obnoxious 98 percent of the time, especially if you say something inane like, as my friend Ellie recently experienced, "Hey girl" or "Hey sweetheart" or "What makes you unique?"

Opening lines in online conversations don't follow the same rules as in real life. Veteran dater Jami says, "You would never walk up to someone in a bar and say, 'I see we both like Pablo Neruda. I'd say The Captain's Verses changed my life. What's your poema favorita?'"

Don't be a dick

It seems really obvious, but thanks to the whole Weinergate debacle, I feel the need to reiterate: Don't send women you don't know pictures of your junk. Tracy Clark-Flory at Salon has a great post about why women don't find that attractive, even women who love you. 

Effort

It's unfair perhaps, but, as Clare says, "Online dating is a woman's game." It's an imperfect world, and the trade-off is we're still making only 70 cents to a man's dollar, among many, many other gender inequities. That said, realize you are going to have to put forth effort, sometimes a lot, to make a good impression, or rather any impression at all on women who sometimes get 10 to 20 messages a week from solicitors. 

A first message that is beyond generic, too brief, or littered with typos will get you deleted right quick. Clare adds, "Read her profile carefully and respond to one or two things in it to establish commonality/shared interests. For example, 'So you like eating out? I love NOPA. What's your favorite restaurant in SF?' I think it helps if you can establish commonality and make a suggestion for the first date at the same time."

TMI

If she has a semipublic online persona, or a blog, read it. Prove that you took a little time to learn about her, and demonstrate that in your message. Caveat: Don't go overboard and don't choose details that are emotionally fraught or show that you've read the last 200 posts she's written. For instance, never lead with: "I hear that you're on antidepressants. How's that working out?" Or, "You love early NIN, became fearful of roller coasters in 2006, and dated lots of Geminis? Me too! Let's grab a frap!"

My Twitter friend Gordon also suggests that men not be too zealous about in-person meetups: "I'd recommend NOT mentioning anything about meeting. If you hit it off over three or more e-mails, then suggest getting a drink."

When to give up

If she doesn't respond to one inquiry, or two at the very most, stop pursuing her. She's not interested. There are extenuating circumstances, of course, like if she has recently gone to prison, or if a new Lady Footlocker has opened recently, but often ignoring someone is the easiest way to convey our lack of interest. Don't be this guy. Give it a rest. Move on.

Alexandra sums up the whole online affair thusly: "Don't be a creep. Don't act like you're god's gift to womankind. Don't objectify the lady. You can't just say 'Hey' and expect us to swoon. Give her a reason to like you. Do bring up similar interests. Be courteous!"

Social media mistress Anna Pulley likes to give advice about how to play well with others on the internets. If you have a question about etiquette involving technology, shoot her a question at AskAnnaSF@gmail.com.

Follow us on Twitter: @annapulley and @ExhibitionistSF or Facebook
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10 comments
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JT Pierce
JT Pierce

Great information!! A lot of guys have a hard time navigating world of online dating, and can come across as creepers pretty easily.  Like you said, it's a woman's game, and men need to learn how to play it, and play fairly.  I just wrote a bit of info on avoiding creeper-dom (http://www.jtpierce.com/how-to....  I think that the more free information that's out there, the better.  That way guys can learn what women are really looking for, and clean up their act a bit.

theTsaritsa
theTsaritsa

I'm thrilled that you used my advice for your column! Wits over tits!

David B
David B

Now how about some advice for those of us who *are* middle-aged men, for whom the idiot twenty-somethings who believe "yur hot" is a formal introduction, have ruined everything for. 

Mike Hawk
Mike Hawk

As a "middle-aged" guy, one who plans to make it to 70 so I guess that's me, the short answer is don't say stuff like the young guys do and you'll already be ahead of the game. I date 20 somethings regularly so I can tell you that it is easier than some would have you believe. Try having a conversation and not staring at her chest to start with and by all means talk about something interesting! Don't start off with Where are you from, What do you do, or Come here often? Boring. If there is something that you feel passionate about and she can relate to, that can make things a lot easier. Ideas? What is she drinking/wearing/doing? I'm not sure if links are allowed so if you don't see one below just google "meet real women online" I have plenty of suggestions on my blog.

meetrealwomenonline.blogspot.c...

Gina R.
Gina R.

I believe she covered pretty in dept how to approach a woman online. Question answered here: "A first message that is beyond generic, too brief, or littered with typos will get you deleted right quick. Clare adds, "Read her profile carefully and respond to one or two things in it to establish commonality/shared interests. For example, 'So you like eating out? I love NOPA. What's your favorite restaurant in SF?' I think it helps if you can establish commonality and make a suggestion for the first date at the same time."

Some men never learn tho I guess, regardless of age haha

loveofmystery
loveofmystery

Interesting. I do have people wanting to add me and followers of my blog who compliment me but I don't add them unless it's someone I've met in person. Didn't know that was becoming "de rigueur" for dating. I suppose if they stuck with the compliments and commenting I might get to know them but mostly I try to keep that separate. 

WhatsYourMystery
WhatsYourMystery

If my blog was as sexually explicit as yours was I would try and keep that separate as well. I believe the vast majority of SF Weekly readers, myself included, need not put up imaginary walls based on the medium of introduction. What's the point in alienating the people who enjoy your work (and maybe even you) based on how you met?

blkensf
blkensf

I still say don't do it. However, if you must solicit women on the internet, this is a guide worth following. 

Beadbible
Beadbible

Great advice, as usual.  People forget that the internet is full of real people.  Pretty much the same rules apply as in the greater society at large.  Many people forget this and want to play fantasy land and lie esxcessively. After a little experience, experience internet users put out that radar to detect creepiness.

Sarah
Sarah

It always amazes me that people need to be told to treat potential dates like human beings. Srsly, don't want to be a creep? Treat her/him like you would like to be treated. 

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