Need some advice.

[JordanRules]

Hello everyone,

I would like your advice/opinions here. Today I was at a local restaurant having lunch with some friends when I saw this waitress in the next section. I've seen her a few other times when I've been in there, and I can't ever take my eyes off of her. No bullshit when I say she could be the twin ****** of Teen Kelly. A petite, blonde, with her hair in a ponytail, and probably the best ass I've seen in a long, long time. I mean she is adorable!

My problem is that I am 38 years old. I would guess her to be in her early 20's. I know she's over 21 because she was serving ****. So, should I try asking her out? Or would she think it's a bit creepy? And being as gorgeous as she is, I can't imagine she would be without a boyfriend. I haven't dated much lately mainly because I haven't met anyone I wanted to know better. Whether she's more my age or younger like this waitress. So, what should I do guys? And girls too. I'd like your opinions, as well.

Thanks for the comments! :thumbsup:

 

[GregCentauro]

What do you have to lose? Go for it! :thumbsup:

 

[Sicario]

Go for it JordanRules, you have nothing to lose and plenty to gain. Just don't make it creepy/stalker type obvious when you go to see her. Try to strike up some small talk to feel her out and if you see that she is sort of flirting with you, then go for the ****. :ak47:

 

[JordanRules]

Thanks guys. I may go for it. Like you both said, I've got nothing to lose, except my pride. But then again, I don't have much of that anyway. So what's to lose? :thumbsup:

I think I'll wait a few days and stop in for lunch. Play in cool. I definately don't want to give off the stalker vibe. She is just so damn cute with a rockin body, so she's probably worth the risk of being denied.

 

[jasonk282]

Nothing to lose, and you don;t have to be over 21 to serve **** etc... just over 18.

 

[JordanRules]

Nothing to lose, and you don;t have to be over 21 to serve **** etc... just over 18.

Really? I didn't know that. Always thought it was 21.

 

[jasonk282]

Really? I didn't know that. Always thought it was 21.

21 to *****, 18 to serve.

 

[~~whimsy~~]

How about seeing if you can charm her first and spark up a conversation? Become a regular there. Make sure you sit in the section, or close to the section, she works in to at least remain somewhat visible. Don't gawk at her, though. Give her a smile or whatever if she walks by you once, maybe twice throughout the whole time you are there.

Instead of being that creepy patron of a restaurant that asked the girl out without any kind of real basis except, Hi, my name is, what would you like to start out for drinks?

Want to go out with me!?

See? Say that in any way you want, how does it sound?

Try and charm her. Don't care how it goes. Don't care about your age. Just see what happens. You have to at least initial a starting point instead of jumping into the whole asking out or whatever.

I could go on and on about how to charm her. Thing is, I don't know you personally, and I don't know her. You will just have to use good judgment. And not to be a critic on yourself or her, especially the age, since you pointed that out as a bump in the road to cross.

 

[jasonk282]

Lots of waitress' flirt to increase their tips as well, not trying to defer you I am just sayin.

 

[jayaprak]

go and enjoy ur best time with her.

 

[~~whimsy~~]

Or... show her a condom, a twenty dollar tip, and say: Yeah. You know you want to, baby!

 

[jod0565]

Strike up a casual converation when you order and throw in something like, "What are you and your boyfriend doing this weekend?" Her response will let you know if she has one or not and will give you the knowledge to pursue her or not.
Good Luck!

 

[Sir Osis of Liver]

im almost 39 and havent screwed a girl over 25 yo ever... dont ask her out u will be labeled a creep... instead get a job there one night a week.. get to know her as a person first then gauge ur chances... but dont pin ur hopes on her... what ive found is that if u are fit and good looking and make good money ur chances are pretty good... with the younger ladies that is...

 

[JordanRules]

Good advice guys. I'm becoming a regular there over the last month or so. And I usually get seated in the section next to hers. I need to ask to sit at a particular table that I know is in her section next time. I'll take it slow and try some subtle conversation each time I come in, until I see what she's like and if she's into me at all. But I know Jason is right when he says a waitress flirts to increase her tips. I'll bet we've all been suckers for that. So, I guess I'll just feel her out for now. And hopefully get to feel her out the way I want to sometime soon. I appreciate the comments guys. Thanks.

 

[Sir Osis of Liver]

lol u said ill feel her out for now! ur plan wont work... ur only a customer and will turn into a creepy customer if she knows u wanna bang her... ur only hope is to get to know her as a friend... get a job there and work with her... if u cant do that than my only advice is to resort to *****.. LOL crack and heroin work nicely.. lol j/k.
get in good shape take care of urself etc... young ladies dont want a fat 40 y/o slob... they want an older man who pays the check and wont cum in 2 min... they wont stay with you but they will brag about u to there girlfriends... which = more young pussy... keep in mind ur just an experience to them..

 

[Facetious]

You're 38 looking like 28 right ? :o She's all yours then :hatsoff:
If not maybe she's got a hott mum... or did somebody already mention that ? :o

Ahh, time flies through your twenties & thirties and it probably goes even quicker through your forties & fifties, point being, for all you young testosterone filled youths... go out and get it now while your still young otherwise the pickens get fewer as you get older.

Me ? I look 15 years younger than reality

Hope that helps

 

[Hot Mega]

Become a regular customer of her's first so she can at least get comfortable with you and possibly get to know you better. Make her laugh a few times with a little charm and wit....then say to her one day (when you're not in a position to embarrass yourself or her) that you were thinking of asking this adorable waitress out named "blah, blah, blah" who's been serving you for how ever many occasions you've been there and you wanted to find out from her what would be the best way to go about doing it and which was her favorite restaurant (make sure she understands you're talking about her by using her name). She'll probably blush relentlessly and if it's a go...she'll do the rest.

Guaranteed to work if she likes you and she's available.

 

[JordanRules]

You're 38 looking like 28 right ? :o She's all yours then :hatsoff:
If not maybe she's got a hott mum... or did somebody already mention that ? :o

Ahh, time flies through your twenties & thirties and it probably goes even quicker through your forties & fifties, point being, for all you young testosterone filled youths... go out and get it now while your still young otherwise the pickens get fewer as you get older.

Me ? I look 15 years younger than reality

Hope that helps

Actually I really do look much younger than I really am. I was even asked for my I.D. when buying some **** this past weekend. Not sure if that's good or bad. :1orglaugh

Become a regular customer of her's first so she can at least get comfortable with you and possibly get to know you better. Make her laugh a few times with a little charm and wit....then say to her one day (when you're not in a position to embarrass yourself or her) that you were thinking of asking this adorable waitress out named "blah, blah, blah" who's been serving you for how ever many occasions you've been there and you wanted to find out from her what would be the best way to go about doing it and which was her favorite restaurant (make sure she understands you're talking about her by using her name). She'll probably blush relentlessly and if it's a go...she'll do the rest.

Guaranteed to work if she likes you and she's available.

That's a great idea you've got there HM! Love it. :glugglug:

 

[Spleen]

It is better to regret something you did than something you didn't do. You have nothing to lose, go for it. Life is too short. Fucking blah blah.

 

[BlueBalls]

Find out where she lives and stand outside her house all night ... in the rain ... staring at her bedroom window. That’s how I got my girlfriend to go out with me, she just doesn’t know we’re going out yet ... or who I am, but give it time, it’s all going to plan. Just as long as she doesn’t call the cops again.

Ahhh, she's a real kidder. But I love it.