Ask DU: When Is It OK to Approach a Woman?

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One Brave Guy Asks: When is It Ok to Approach a Woman

Before we jump into this post, we have a little announcement to make! Many of you have been asking if we’d consider doing an ‘advice column’ of sorts within our blog. While we may not be Dr. Phil, we do love to help others! With that in mind, we are now officially taking questions!

First up? An email we received from one of our male readers:


I was wondering if you could give me some advice on approaching women. I’m a pretty big guy – 6’8” and 380 pounds, and I normally clam up at the thought of trying to strike up conversation with women that I don’t know.  

A few weeks ago I was at a bar with some friends. I was having a good time and noticed a girl at the other side of the bar looking at me. I had a few drinks in me and was feeling confident, so I decided to take a chance and approach her. I asked her to dance… and she responded by exclaiming, “EWWW oh my god, I would never dance with you! You are fat and disgusting!” Needless to say, this was a huge blow to my confidence and now I’m hesitant to approach any more women, especially since this is the second time something like this has happened.

My question is – from a woman’s perspective, how can I know it’s safe to approach? Is there a way to test if she’s interested before I open myself up to rejection?




 Joe wants to know when is it ok to approach a woman…

Lisa’s POV:

First of all, a little perspective: just be glad you’re not the man who has to deal with a bitch like that for the rest of your life. Bullet? Dodged. Girls with a nasty attitude like that are the exception, not the rule – well, unless you’re in River North (lol). Most times, if a girl isn’t interested she’ll simply provide a polite excuse – a fictitious boyfriend, a long day at work, or will simply say “Sorry, I’m just here to hang out with my girlfriends!” Or if she’s like Laura, she’ll whip out a fake engagement ring… #TrueStory

Coming from the ‘shy girl’ perspective, I don’t display any “cues” or obvious signs of interest – no matter how much I like someone. With that in mind, I would say the best thing you can do is test the waters first. Find a reason to get in her vicinity (for example, if she’s at the bar, stand near her and order a drink). Find something neutral or funny to comment on (a game on tv, a unique beer on tap, etc.) and see how she responds. For example: “Man, have you been watching this game? Blahblah DA BEARSSS blah.”

If she’s open to talking, she’ll smile and offer a friendly response – even if she doesn’t give a shit about sports. However, if she wants to be left the f*ck alone, she’ll be evasive, short, give you the brush-off or avoid eye contact. In that case, move along. Oh, and if you’re not naturally chatty, make sure you think of what you’re going to say next (if she responds positively) so there’s not an awkward silence while you wrack your brain for something else to say.

Oh, and PS: I’d avoid asking girls if they want to dance unless they’re already on the dance floor. Not everyone likes dancing (i.e. your chances of getting rejected go up) and I think there’s a perception that many guys want to dance solely for the physical contact. But then again, I hate dancing and got humped one too many times at Nitro back in high school, so…


Gina’s POV:

I’m with Lisa on this, homegirl is the exception and unfortunately it happens. As for approaching someone, it really depends on whether or not the girl is smiling at you and locking eyes or not (at least with me it does). While I may not actually approach a guy I’m interested in, I will definitely try to get his attention by making eye contact and smiling.  This is supposed to work, but honestly I think I’m smiling at the wrong guys because it’s rare that they actually approach. Hmm… maybe I’m not the best one to ask about this since I seem to need advice myself.

You may not want to hear this, but sometimes you just have to make your way over and give it a shot. Don’t be overly aggressive or all “Broseph” about it and any ‘good’ girl will respond in a respectable way. If she isn’t, then really she’s not worth your time and you lucked out. No one wants to date a bitch, do they!? But please…. please, please, please (!!) be yourself. I’d appreciate that more than you telling me you’re the manager for some hot-shot basketball team in town for a game. While I might not immediately think to verify whatever line you throw at me, I assure you my friends will and you’ll be called out on it. (True story, I heard it on the radio – HA!)

Don’t let one chick ruin it for the rest, from a shy girl to a shy guy, I have to believe we’ll meet the right person. It might just take a bit more work.




Brandy’s POV:

Yeah, Joe, ditto on what Lisa said. That girl’s not getting any points in the cool school. I understand; it can be hard out there when the guy is traditionally supposed to approach the girl, and this generation has done well in producing a nice subset of mean girls, so you never know what you’re going to get.

But if you’re dealing with an outgoing girl like me, you can sit back and relax – we usually do the approaching, which looks more like obvious, aggressive eye contact, that says “Hey you, yeah you, I’m ready and waiting for you to saddle up and talk to me – get over here STAT!”  or maneuvering ourselves to be near you to order a drink  (“Oh, hi! How did that happen that we would end up by each other?!”) Be cautious with the subtle eye contact though, sometimes that could be the other person trying to figure out if she knows you or wondering why you keep looking at her. If you take that as a green light, you could be misinterpreting.

This point is where a wing man comes in handy. Make sure she’s with a friend, have an obvious reason to approach her, and you and your boy can then strike up conversation. Jokes and compliments are easy wins, ex: “Those are really cool shoes you have. I was noticing them across the bar!” takes you out of stalker category and suddenly you’re four drinks in and she’s telling you stories of her childhood. This gives her time to get past any initial prejudices to see the real you, which is probably a pretty kick-ass dude.

Or just speak French. It always works for me.

Oh, and next time you get that type of response, I’d come back with something like this:

“You know, I take that back. From across the bar, you seemed to be a really cool girl, someone who is not pretentious and stuck-up on themselves. But now that I’m closer, I see the truth. You really suck as a human being. You have a good night, ma’am.”

— heart

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