Love a waitress

[TravelerJoe22]

I have a question for waitresses or women in general. I am an older (50's) man, single, who is financially well off. My Mother was a waitress and I saw how hard she worked, and it gave me an appreciation for what these women do. Lately I have found that I enjoy a friendly banter with my waitress when I am eating out and that these younger ones always seem to show more and more cleavage. I am sure it is just to get more tips, but it is very provocative. I love to travel and find myself wanting to be spontaneous with a waitress and ask her to go on a weekend get away with me. I am always generous with my tips (30 to 40%) but do not try to get the same waitress every time I go to a restaurant. How does someone my age ask a 20 something woman to take a weekend island vacation with me?

Traveler

 

[SassySheDevil]

First off. Most servers would either laugh at you, or not take you seriously if you proposed that as a stranger. I can only believe that the only person desperate enough to take up such an offer from a stranger, is someone with a death wish. You say that you try and get different servers, so you are not forming a relationship with them. I don't care if the hottest guy on the planet walked in and asked me for such an offer. I'd be like "hell no" then go cry behind the counter. A server may go joke about it behind the counter to her co workers, but only a crazy person would take up anyone on such an offer.
Now if you form a relationship and become a regular with someone, that could be totally different. But some random young server with tits, not as likely. It took me some time to form a "relationship" with many of my customers. Depends on how often they engaged in conversation, or how often I saw them.
But I will say that the one thing that always made my day better, was the little notes that were left on napkins, receipts etc. To this day, I have every one of them in an envelops in my safe.

Good luck in the fantasy though. Maybe you'll get lucky and find Miss Desperate death wish girl.

 

[_Lorelei_]

I would say you're better going on a dating website and advertising that you want to date someone who works as a waitress, rather than trying to pick someone up who is just trying to do their job

 

[TravelerJoe22]

Good idea

Thanks for the input! I'm not a creepy guy, just maybe a little shy and naive! I like the idea about the notes on napkins. I do engage them in conversation while they are waiting on my table. Nice to know they may think I would do them harm if I just asked them!

 

[SassySheDevil]

Waitressing isn't like the movies. No one comes along and offers you a lottery ticket. Thanks to the movies, everyone jokes about it though. So when someone comes along and offers you fantasy, you just smile and walk away. But yes, it would very much scare most.

 

[kristaswallows]

You are not unique in being an older guy who likes cute girls who bring them food and booze. But as long as you think of me as a waitress, I probably think of you as >30%.

 

[coacheric]

Stopped and had lunch yesterday. I was by myself and normally just grab carry out but really wanted the down time from driving so I ate in at a sports bar. The waitress was a young super cute woman that called me sweetie and hon the whole time. Always made eye contact and all around drove me crazy. She got a good tip and I left.

A good waitress knows how to get a good tip out of you. Enjoy the attention and move on with the day.

 

[Sir Victor]

Hmmm, interesting question, I think it depends a lot on your charisma/personality, looks and if you get a waitress who might have a thing for older men. As others have suggested I'd say become a regular with one that is extra nice to you then try to subtly find out if she has a thing for older men.
Are you looking for sex in this or just a companion?

 

[Deckr]

Gotta say, leave the poor girls alone. They're just trying to do their job. They don't need random strangers trying to pick them up while they're working.

 

[legally_non_blonde]

simply ask...what's the worst? she will say no and you move on...at least you won't have the regret of not even trying

 

[kaitlyn_sun]

I immediately get the appeal of this... it's a well-worn fantasy, and the fact is, it's something that waitresses don't really have a choice but to play into. it's part of their job.

but it's still a fantasy. nothing fucks up a person's game like trying to apply fantasy rules to the realities of actual relationships.

but seriously... one of the miracles of living in the future is there's a website for everything now. it used to be impossible for young gay kids to find each other, now grindr is a thing. if you're an older gentleman looking for a young woman interested in taking a vacation with you, then just go here.

boom. no mystery to solve. you can even specify waitresses if you want.

 

[CarnivalBarker]

I wait tables part time and weekends. Hit on ALL the time, and I totally play into it. Every man who thinks he has a chance tips way more than every man that doesn't. And I'm not stupid.

 

[Que Va]

I could write this story but it would be fiction, mostly. People click or they don't. Looking for love where people are looking for tips is a fools errand. Been that fool with mixed results.

Thanks for the input! I'm not a creepy guy, just maybe a little shy and naive! I like the idea about the notes on napkins. I do engage them in conversation while they are waiting on my table. Nice to know they may think I would do them harm if I just asked them!

A note on a napkin plays into the creepy guy role. Don't unless it is an (accurate) observation about her role as a server. Even better if you hand that to her boss. I've had a word with a boss after someone made me feel great and am not shy about the fact that her being cute and warm and flirty made my day. She sees you talking to the boss, he is smiling at her, you leave.

But really you are going to have to sell yourself in person while you are still there. If you leave a note, it will be appreciated and giggled about. Then they are all going to try and work you and no one needs that expense.

You are not unique in being an older guy who likes cute girls who bring them food and booze. But as long as you think of me as a waitress, I probably think of you as >30%.

This is key. "I always liked waitresses" (I like dental hygienists) will not work. She might be an outstanding waitress, might take justifiable pride in it, and genuinely love the people she works with (doubtful) and most of the customers (that tip well) but SHE doesn't see herself as a waitress first, so if you do, you are dead. Figure out something about her. I have better luck with the few seconds with cashiers than waitresses but the same idea applies. Just like sales. Start with the name, hopefully it isn't Ashley because it is hard to tell and Ashley that her name is fascinating given there are so many. Does she have a slight regional dialect? If you have to, surely her eyes remind you of someone...work it. Like she is an actual girl.

Gotta say, leave the poor girls alone. They're just trying to do their job. They don't need random strangers trying to pick them up while they're working.

Agree and not. They don't like people assuming they are going to go home with them for a $20 tip. They don't like it when you appear to be showing off for your friends by chatting up the waitress. If you come in alone, they know that by definition at that moment you are lonely. It is OK to reach out. It is Ok to be funny and charming and even flirty. Needs to have a veneer of plausible deniability. You almost cannot actually ask them out so I agree with the trying to "pick-up" part. Of course you are trying but it needs to look like you were not trying. Which is why it is nigh impossible. You have to lay some groundwork and you have to let her decide to linger at your table for conversation. If she is not getting dirty looks from her boss, she is not into you. No waitress ever minded Cary Grant acting bemused, yet enthralled in their station.

Bartenders are even harder. I have ever even gotten so much as a sincere flirt out of one. They are fending off drunks right and left, so treat cocktail waitresses like bartenders and don't be an amorous drunk. Any service worker who is paid to smile at you is a challenge. The challenge is to find a reason for them to smile with you like it isn't their job.

 

[Sir Victor]

I eat out a lot and I have a lot of girls in their 20s flirt with me all the time, or just be extra friendly. I've always been a good tipper. I tip more if they are just pleasant and polite since it makes for a better experience. I don't expect them to go out with me just because I'm a good tipper. I think that 30 to 40% as you do is a bit over the top, 25% is considered a very good tip. I do tip closer to what you say when I'm eating light and alone where it is a very minimal bill.
Oh, and you don't know how often they are left really bad tips, how about 5% on a $200 bill didn't believe it until she showed me the receipt. Some leave $1 no matter what, or round up the change. But, you might be surprised what generous people do for a server that they've gotten to know over 5 or 10 years of going to the same place. They almost become like family.

I've had a few friends tell me that they get better service when they are with me and they suggest that it is something about me, lol.