How To Ask A Guy Out On A Date | Stranger Edition


Looking to find out how to ask a guy out on a date? Specifically a guy you just met?  Well you'll love this week's episode where we discuss a simple yet charming way to ask someone out on a date.

Now if you're a woman who's uncomfortable with asking him out (i.e. "I'm not asking a man out.  He should ask me out.")  Stick with me because you may find you like this particular technique.  

Trust me it's subtle enough to be considered a suggestion, but clear enough to land a you a date.


If you haven’t caught the episode on How To Approach Any Man Anywhere the tips detailed there will help greatly with this step.  But to initiate the approach here are some TLM Cliff Notes:

  • Say something relevantly witty. (No need to be a comedian, you’re just looking to make him smile)
  • Make sure you’re smiling and displaying open body language.
  • Ask him a question or make an observation.
  • Drop him a compliment that he didn’t expect. (everyone likes a compliment!)

This should be plenty to get the ball rolling with small talk, so make sure to keep it light, fun, and friendly.



From what you can tell you like this guy.  He seems friendly, easy to talk to, and it certainly helps that he’s easy on the eyes.  Now’s the time to pay attention to your window of opportunity.  

The perfect window of opportunity is usually a couple paces before interruption or a change of action.  

So if you're at a grocery store or a gym your window of opportunity is before your handsome stranger moves to the checkout line or to another piece of equipment. If you're in line at a Starbucks, or say a chipotle, you want to make your move 1-2 people before he gets to the order clerk.

This is simply because once a person is interrupted or begins a new task, their focus (on you) is broken and you'll have to compete with whatever it is they actually came there for.


You’re inside the window of opportunity and desperately want to make a move.  Now’s a perfect time to thank this charming gentleman for the brief conversation and tell him how much it made your day.

“Thanks so much for talking to me. It’s definitely making my time in line much more enjoyable."

If his response is favorable - he's still smiling, he agrees, his body language is open and he's making eye contact, go for the final step.


Bring it home by telling him again how much you enjoyed talking to him and how you dare not miss the opportunity to get to know him better.  Then subtly suggest a date.

"Hey it really was refreshing to chat with you and honestly I’d be kicking myself if I left here without telling you that it’d be really nice to see you again. You seem like a really great guy. Maybe if you're single and or available we can meet somewhere on purpose and have a longer conversation."

If he agrees CONGRATULATIONS!!! You just got yourself a date!!!! My suggestion is to give him your number but not take his.

This allows you to sit back and still let him pursue you. If he doesn't call it's ok, don't get all worked up or go into depression.  just try the technique another time with another handsome stranger.


There you have it, a simple yet charmingly effective way to ask a guy you just met on a date.

If you liked this episode would you please hit the like button?  And because sharing is caring do make sure to pass this on to anyone you think may enjoy it.

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You can have the love you want.  Sometimes you just have to do something different to get something different.  And if you’re willing to do the work, I’m more than willing to help you get there.


Wishing you small talk, bright smiles, and butterflies,