Plenty of opportunities, bad timing

Submitted by Centered on
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I can never seem to find the right time to make an advancement on a female. It always seems inappropriate, no matter the situation I'm in.

A couple examples: If I try something at work then I can potentially get terminated for sexual harassment and/or have my reputation ruined. Asking out the cash register girl at my favorite food place in front of several waiting customers seems wrong and putting her on the spot.

Am I just overthinking this too much?

People at work

date each other a lot. I don't see how asking someone what she likes to do when she's not working would get you into trouble. Movies? Her favorite kind of restaurant? Whatever? Then next time around you could suggest getting together to do that activity. If she says "no," drop it.

Why not pass the cashier a note with your phone number and a lighthearted invitation to call you.

go for it

Talk to the girl at the register...I always ask people at their employment: Am I going to get you in trouble if I try and talk to you? Then I have a conversation, while they do their job. I definetly got the # of a girl working at dominos;
Also what are you saying to women when you ask them out? it can not be sexual harassment if you do not say something sexual. Take a big breath, count down from three to 1 in your head (thats what I do when I get the jitters), walk over, and just say: "Hey___, I have noticed you around the office for a while. if your are not doing anything on Monday, we should get something to eat"
I say things I would find funny like.... Let me take you out and take care of you. or let me feed you.... whatever works 4 u

A statement usually works

A statement usually works better than a question. So instead of "do you want to go out for a drink/bite with me?" you can just say "hey, you're fun, let's hang out for a drink/bite!". Besides sounding more assertive, this way of putting it also makes it less prone to rejection since it doesn't directly invite a yes/no answer.

If you're having with a girl by just chatting and flirting, you can always say that you want to hang out with her.
Good luck and keep us posted :)

Thanks for all the

Thanks for all the suggestions! I am definitely being over cautious, I'll work on that.

Another issue I'm facing is I'm around that age where it's hard to tell how old a girl is. I'm 21 and I swear these 16-17 year olds look much older than they are, lol.