Should I Approach Them? A Handy Guide

You’re completely over your approach anxiety and you spot a cutie you want to chat up. Problem is, you’re not sure if it’s okay to approach them. Well, here’s a handy guide:


If it’s during Rush Hour, HELL NO. Are you kidding? They’re listening to the Tao Of Indifference podcast and you’re killing their vibe. If it’s any time after that, it’s a maybe but most likely no.


This one is also a maybe. Make sure asking them out doesn’t represent a conflict of interest or a potentially awkward working situations.

They’re in the Service Industry and I’m at their workplace

Go for it, but read the situation carefully and don’t be pushy. They might just be being very polite and charismatic and not flirting. Tip them even if they reject you!

Bar or Club

Absolutely, but again, read the situation carefully and don’t be pushy. If they look like they’re making out with someone, maybe avoid hitting on them? Some controversial advice for guys: Don’t buy drinks for randoms at bars or clubs. There are better ways to show you’re a stand up guy without buying a stranger a drink.

Library or Bookstore

Maybe, but you know, do it quietly unless you want to get shushed.

At a Concert or Show

Absolutely! As long as they can hear you.

The Gym

Unless they strike up a conversation with you, or seem to be smiling or looking in your direction, I’d avoid hitting on someone at the gym. Don’t offer to show them how to do an exercise unless you’re a personal trainer.


You know, my Dad met my Mom in an elevator,  so you know what, go for it. I wouldn’t be here otherwise and I’m pretty awesome.

You’re both on line waiting to order food

This one is a suggestion from my girlfriend which I didn’t even consider so I’ll just quote her:

“If a guy noticed me while I’m waiting to order a salad, and makes small talk, if i were single I’d totally take the bite. Plus, it’s very likely he is employed if he’s getting lunch when people usually go on lunch break”

Remember, if they reject you, or you think they’re giving you a fake number, keep it moving and be indifferent.

Good Luck Out There.

2 thoughts on “Should I Approach Them? A Handy Guide

  1. Even if it may not be the most appropriate of time to approach someone, if you really like the look of them, I’d say just go for it. It may cause something awkward, but at least then you’ll know its a no. and I’m sure both parties will get over it within a few minutes anyway


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