So as the title says, there is this waitress i want to ask out. im celebrating my 21st with friends soon (no drinking, just having a good time) and i think that is a good reason to ask her out. thing is... im not very confident and i know i will be nervous. my friend and i usually go to this restaurant every monday and she is really cool and even if she isnt our waitress she comes up to chat with us so she isnt just nice for tips. i like her but at the same time i dont know if i will like her outside of the restaurant because i dont know how she really is. but i guess thats all the more reason to ask her right? haha i was wondering if any of you guys have any advice on asking a girl out? i have done it before but that was when i was younger and i knew the girls a while before i asked them so i was more comfortable with them. im wanting help asking out a girl i barely know. how do i seem confident? what should i wear? thinking about an unbuttoned button down with undershirt, jeans, and some nicer shoes. might wear a baseball cap as well because i usually do. i hope if she says no she wont go a blab to the rest of the staff that i asked her out. now THAT would be embarrassing! lol

thanks in advance

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First off, you're over-thinking it and if you continue over-thinking it, you WILL fail.  Just approach it for what it really is, NO BIG DEAL.  If she rejects you, you move on.  Don't take it personally.  

As for asking her out, just tell her "hey, let's get a cup of coffee or a drink sometime. What's your number?"  Ask her this casually after you go through the whole standard lines "hey, how's your day going blah blah blah.....".  Just say it confidently and before you do, remind yourself that it is OKAY to be anxious or nervous.

Don't worry too much about dress. Just don't look like a slob. Try to talk to her just like anyone else, but as always be charming and playful. If she's having fun talking to you or serving you at the restaurant, there's a good chance she'll think she could have fun on a date, too.  If this seems to be going well, write down your number and give it to her.

If she doesn't call, don't take it personally. Waitresses probably get several phone numbers every day.

Easy- say "What are you doing after your shift? If its OK with you,  I would like to take you out somewhere".  Done.

That's generally a good sign. 

hahaha thats funny. i wish.

Sometimes you just have to go for it, and don't worry to much about come across as nervous or awkward, a lot of girls kind of like it. I suppose they think is shows you like them or your not a player or some such.

makes sense. i have actually heard that some like it. heard some think its cute. but then again i never really wanted to be associated with the word "cute" ive always wanted something more manly. and im not just saying that because im on this site. lol but im afraid that at the end of the day im alright with being "cute" if it gets me the girl. 

nothing wrong with cute if it gets your foot in the door

Manly advice of the day:

 Don't use "lol".  

Walk up to her and ask her, in a humorous and light hearted (but confident) tone, "Let's say I really want to ask you out, but since I only run into you while you are working I'm not sure if it's okay to approach you with it. What's your advice? "

"Let's say I really want to ask you out, but since I only run into you while you are working I'm not sure if it's okay to approach you with it. What's your advice? "

Unless you're uberconfident, I would advise against this. Women can detect when a man is uncomfortable or nervous when he's trying to make a move (and they can often see the move coming from a mile away). Trying to be suave when you're not naturally inclined to it is a setting yourself up for failure. 

haha i....might just do this! thanks! 

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