Get SF Weekly Newsletters

Thursday, June 9, 2011

Pick Up Women Online Without Being a Creeper

Posted By on Thu, Jun 9, 2011 at 7:30 AM


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).


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. 


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."


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

Follow us on Twitter: @annapulley and @ExhibitionistSF or Facebook
  • Pin It

Tags: , ,

About The Author

Anna Pulley


Subscribe to this thread:

Add a comment

Popular Stories

  1. Most Popular Stories
  2. Stories You Missed

Like us on Facebook


  • clipping at Brava Theater Sept. 11
    Sub Pop recording artists 'clipping.' brought their brand of noise-driven experimental hip hop to the closing night of 2016's San Francisco Electronic Music Fest this past Sunday. The packed Brava Theater hosted an initially seated crowd that ended the night jumping and dancing against the front of the stage. The trio performed a set focused on their recently released Sci-Fi Horror concept album, 'Splendor & Misery', then delved into their dancier and more aggressive back catalogue, and recent single 'Wriggle'. Opening performances included local experimental electronic duo 'Tujurikkuja' and computer music artist 'Madalyn Merkey.'"