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Where (And Where Not) to Try Approaching a Woman

The advent of online dating has taken some of the challenge out of approaching someone to whom you’re attracted. Once upon a time, if you saw an attractive woman in public, you couldn’t scurry home and post a “Missed Connections” ad on Craigslist or frantically Google “girl+blue dress+works near the CVS” and hope you stumbled across their social media profile.

No, you had to walk up to her, introduce yourself, and make your pitch. This is what I call “stranger game”; that is, the ability to walk up to someone you’ve never met and say just the right things to make them interested in you, all in the span of two minutes. The idea of walking up to a complete stranger and forcing her to talk to me sounds like a nightmare for everyone involved, but I get that some of you like to do things the old-fashioned way.

Now, I may not be very adept at approaching a woman in public, but I have a good idea of which behaviors are appreciated and rewarded by women and which are frowned upon by women and/or your local police force. So if you’re the go-get-’em type, then at least allow me to dispense what wisdom I do have. First things first:

Where You Approach a Woman Matters

The main thing I hear from a lot of women isn’t that they don’t like being approached; rather, it’s that they don’t like when a guy just barges into their life like a silverback gorilla on coke. There’s a way to approach a woman without being intrusive or slightly menacing.

Unfortunately, because so many guys opt for the aggressive approach (“HARD SELL, BRAH!”), women have to be just as aggressive in spurning the advances of men. Naturally, this poses a problem to the polite, normal guy who just wants to strike up a conversation. But while there’s nothing you can do to improve the odds that she’ll like you, there is one factor that dramatically impacts the odds that you’re being an unwelcome interruption into her daily life: your location.

And remember: no matter the venue, she has every right to tell you to hit the bricks. A lot of guys feel like they should get credit for either A) working up the nerve to approach a woman, or B) for taking the time out of their day to approach her.

But here’s the thing: you’re not actually obligated to approach her – you’re doing it because you want to do it. You’re already placing your own wants over hers, so the least you can do is make your attempt as minimally-invasive as possible. So with that in mind, let’s look at a few places and assess whether approaching a women there is a good or terrible idea.

At a Bar

Odds She Won’t Mind: The odds here are pretty good, since a bar is a place where people go to socialize and meet new people. (Why yes, I did just explain the function of a bar. Where are you going?)

If a woman is at a bar, she’s at least aware of the possibility that a guy might approach her. She may not be interested in talking to you, but given that it’s a social setting, you’re at least minimizing the degree to which you’re disrupting her day.

About the only thing you shouldn’t do is walk up and act like an asshole. Nobody likes a dick.

On the Subway

Odds She Won’t Mind: Unbelievably low. Approaching someone on the subway is not only intrusive, but you’re probably going to make her extremely uncomfortable.

A subway is a confined metal tube that primarily rides on rails inside a larger, dark, concrete tube. Unlike the outside world (we mole people call it “The Bright Land”), if an interaction takes a bad turn, there’s nowhere to go. You’re stuck with that person.

Approaching a woman on the subway not only disrupts her day, but it also tells her one of two things: either you don’t understand that it could make her uncomfortable, or you know and simply don’t care. In either event, you’re not exactly putting your best foot forward.

On the Sidewalk

Odds She Won’t Mind: Again, pretty damn low. While it’s true that the sidewalk is a less-menacing venue to approach a woman than the subway, it’s no less intrusive.

Pop quiz: Why do people walk on sidewalks? Because they’re going somewhere.

Stopping a woman on the sidewalk just to say, essentially, “DURR UR HOT” is pretty rude. Because what you’re really saying is “Hey, I’m sure you have somewhere to be, but my boner wouldn’t have let me live it down if I didn’t block your path to throw unwanted compliments at you and make you late for your actuallife.”

In Line

Odds She Won’t Mind: It’s hit-or-miss. If it’s a line for something out of the ordinary (a concert, for example), striking up a conversation isn’t a terrible idea; after all, you both have this thing in common.

On the other hand, if it’s a line for something run-of-the-mill like the bank or the Post Office, it still falls within the bounds of her normal, everyday life, and your approach is still an intrusion. (Besides, what the hell are you gonna say to someone in line at the Post Office? “Picking up a package, huh? Oh, you’re mailing one? Wow, I didn’t know you could do that.”?)

On Social Media

Odds She Won’t Mind: She will, because it’s unfathomably sad. Don’t be one of those guys on Instagram who follows models and comments on every photo like “PLEASE LET ME KISS YOU I WOULD BUY YOU NICE THINGS [15 consecutive rose emojis].”

In a Club

Odds She Won’t Mind: She’s at a club. I sincerely doubt she’ll mind.

The good news here is that clubs are packed with people who have absolutely nothing to say of any substance, so you can pretty much blurt whatever pops into your skull. Either she’ll like you, she won’t, or some random douche will punch you for no apparent reason.

Clubs are the worst.

A final word of caution: even if you’re polite, friendly and not-at-all aggressive, you still stand the risk of rejection. Just because you’re interested in a woman doesn’t mean she’s obligated to drop everything she’s doing and welcome your intrusion upon her life with open arms.

Some people, male and female alike, don’t mind the (hopefully well-intentioned) interruption; others do. That’s the way of the world. So if she blows you off – and unless you’re Bradley Cooper, she probably will – thank her for her time, apologize for the intrusion and, most importantly, let her get on with her day.

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