Flirting with Bartender

[Minneapolis]

It’s been quite a few years since I’d been to the Gay 90’s, but about a year ago I went back and immediately developed a crush on one of the bartenders. He looks a lot like someone I used to be attracted to. I’m pretty convinced he’s straight, but he definitely knows how to work a crowd and get tips. He’ll wear very revealing outfits, short shorts, briefs, etc.

The first time I met him, I tipped well and gave him my phone number. Nothing came of it, which I expected. A year later I went back and was shocked that he remembered both my name and my drink (Jack and Coke). Later I found out he had actually kept the note with my name and number by his station so he could remember customers. I assume he does that with other people too.

Since then, I’ve stopped in every few weeks. He always has my drink ready, remembers my name, and is very friendly. I tip well—usually $20 for a couple drinks, and sometimes another $20 on the way out. Not outrageous, but definitely above average.

Today something happened that completely caught me off guard. I was walking around Uptown and suddenly heard someone call my name. It was him on a scooter. He stopped, got off, gave me a big hug, and we chatted for a few minutes. He asked if I lived nearby, told me he was on his way to get a tan, and when we were done talking he said, “I hope to see you this weekend.”

Now I’m on cloud nine, but I’m also trying to stay realistic. He’s a very attractive guy in his 20s. I’m a guy in my 50s. I’m 99% sure he’s not romantically interested in me and that he’s simply friendly and appreciates a good customer.

What I’m struggling with is figuring out how to interpret the off-the-clock interaction. Bartenders remember regulars, but stopping, getting off the scooter, giving me a hug, and chatting felt different than normal customer service.

For those of you who have worked in bars or have been regulars at bars, how would you read this? Friendly bartender who recognizes a good customer? Something else?

Also, separate question: Is it inappropriate to ask a bartender whether he does any kind of private entertainment, appearances, or paid work outside the bar? I’ve had no problem asking dancers or strippers that question, but asking a bartender feels very different.

 

[CuriousByNature]

3 minutes ago, Minneapolis said:

 

It’s been quite a few years since I’d been to the Gay 90’s, but about a year ago I went back and immediately developed a crush on one of the bartenders. He looks a lot like someone I used to be attracted to. I’m pretty convinced he’s straight, but he definitely knows how to work a crowd and get tips. He’ll wear very revealing outfits, short shorts, briefs, etc.

The first time I met him, I tipped well and gave him my phone number. Nothing came of it, which I expected. A year later I went back and was shocked that he remembered both my name and my drink (Jack and Coke). Later I found out he had actually kept the note with my name and number by his station so he could remember customers. I assume he does that with other people too.

Since then, I’ve stopped in every few weeks. He always has my drink ready, remembers my name, and is very friendly. I tip well—usually $20 for a couple drinks, and sometimes another $20 on the way out. Not outrageous, but definitely above average.

Today something happened that completely caught me off guard. I was walking around Uptown and suddenly heard someone call my name. It was him on a scooter. He stopped, got off, gave me a big hug, and we chatted for a few minutes. He asked if I lived nearby, told me he was on his way to get a tan, and when we were done talking he said, “I hope to see you this weekend.”

Now I’m on cloud nine, but I’m also trying to stay realistic. He’s a very attractive guy in his 20s. I’m a guy in my 50s. I’m 99% sure he’s not romantically interested in me and that he’s simply friendly and appreciates a good customer.

What I’m struggling with is figuring out how to interpret the off-the-clock interaction. Bartenders remember regulars, but stopping, getting off the scooter, giving me a hug, and chatting felt different than normal customer service.

For those of you who have worked in bars or have been regulars at bars, how would you read this? Friendly bartender who recognizes a good customer? Something else?

Also, separate question: Is it inappropriate to ask a bartender whether he does any kind of private entertainment, appearances, or paid work outside the bar? I’ve had no problem asking dancers or strippers that question, but asking a bartender feels very different.

 

It sounds like he clearly appreciates you.  I would be wary about asking about other types of appearances or services outside of the bar, in case he becomes offended and it ruins the rapport you both enjoy.  Perhaps it is best to play it cool and see where he leads things, or if he leads things?  I'm the least overt person on the face of the planet, so maybe my advice is too cautious.

[nomad]

He is in the service business and doing his job well.  Would suggest not to read too much into things.  Allow him to make the first move if he's interested.  A more casual way would be to maybe ask if he would like to have coffee sometime when he's not working.  It's brief and harmless on the surface.  I find dinner dates can be torture if the rapport isn't there.  Lunch and coffee are a lot less of a time commitment and offer a ready off ramp.  "This was nice.  Thanks for meeting me.  Let's talk soon."  Then RUN as soon as you're out of sight.  🤣

 

[BigDMike]

I don’t want to be Debbie Downer….and I’m not a bartender…but I did date one…a gay one…though….and in essence all these things make him good at his job and get you to tip him well for a pouring jack and coke in a glass.  People that are good in the service industry use their skills to earn more money…that’s after all the only way they too can make more money.  I would just say….enjoy the attention but don’t get over fixated on it unless he leads you to something outside of coming to the bar and putting more cash in his pocket.  The bartender I dated used to be really flirty with everyone and at first I thought it was just with me….then we started dating and I watched it continue and come to find out…he’s like “Well yeah..how do you think I keep the big tippers coming in” 

 

[MikeBiDude]

I’d suggest go with the flow and let things unfold, don’t push. I’ve had a couple of these seemingly improbable situations work out into a bit more.

I would not recommend asking about “private entertainment”

[+ purplekow]

Next time you go simply ask:   If I gave you my phone number again, would you ever use it?   He could be coy and say something like, give to me and find out. Or he could just say yes or no.  If instead he asks why do you ask, be honest and say you would like to get to know him better.  Victory goes to the bold and so just ask and if the answer is no, you can continue to fantasize and if the answer is yes, well then give it to him and wait and see.  

[moonlight]

I'm apparently the resident wet blanket on threads like this. But based on what you wrote I wouldn't read anything into it beyond a friendly guy who appreciates his regular good tippers and knows how to keep them happy. He already had your number and didn't do anything with it. He knows you'd be interested. He would give you his if he wants more. Enjoy it for what it is. Your instincts are right that he's just doing his job, though likely in a genuinely warm and friendly way. The street interaction doesn't come across as anything other than a friendly greeting while seeing you out of your usual context.

[+ purplekow]

6 minutes ago, moonlight said:

I'm apparently the resident wet blanket on threads like this. But based on what you wrote I wouldn't read anything into it beyond a friendly guy who appreciates his regular good tippers and knows how to keep them happy. He already had your number and didn't do anything with it. He knows you'd be interested. He would give you his if he wants more. Enjoy it for what it is. Your instincts are right that he's just doing his job, though likely in a genuinely warm and friendly way. The street interaction doesn't come across as anything other than a friendly greeting while seeing you out of your usual context.

Some pursuits end in a capture and some do not.  Not pursuing  is a guarantee no.  Do not be creepy or pushy but subtly ask and the answer will be obvious.  To me, it is not obvious now.  

[Minneapolis]

Thanks for everyone's advice.  I'll stop by this weekend and see where the conversation goes.  

[nomad]

Yes don't follow the Don't Ask, Don't Tell route.  Ask in a casual way.  And Do Tell us what happens!  😀🤞

[TonyDown]

Not calling your number could have been him just being careful, perhaps not interested mixing business with pleasure.  One might might wonder how many customers hand their number, hoping for a quickie with a cute bartender.

If he came up in public to hug you, that might have been a good opportunity (away from work) to ask him for coffee.

Since he asked if you lived nearby, one might have responded, "yes, how about you?  Do you live in Uptown?"   And so on.    

 

 

Edited June 15 by TonyDown

[wsc]

15 hours ago, purplekow said:

Some pursuits end in a capture and some do not.  Not pursuing  is a guarantee no.  Do not be creepy or pushy but subtly ask and the answer will be obvious.  To me, it is not obvious now.  

As has been said, You miss all the shots you don't take.

[Guest]

This thread reminds me of a twink who used to work at a fast food place near where I lived. He reminded me of the twinks I always chase on RM. However, he was genuinely sweet and smiley, like I used to be. Like another client always says on here, I took it as him looking for his Pretty Woman resolution. However, it felt great in the short time he worked there. It was definitely a significant (albeit fleeting) boost to the ego. Unfortunately, he quit, and I never saw him again. This was last year. (And heck, I never tipped him.)

[ACluelessGent]

On 6/15/2026 at 12:49 AM, Minneapolis said:

Friendly bartender who recognizes a good customer? Something else?

Professional who recognises revenue generating opportunity.

On 6/15/2026 at 12:49 AM, Minneapolis said:

Also, separate question: Is it inappropriate to ask a bartender whether he does any kind of private entertainment, appearances, or paid work outside the bar? I’ve had no problem asking dancers or strippers that question, but asking a bartender feels very different.

 

Don't. Its vulgar and unnecessary. He knows money is involved. Ask him for a coffee or a drink and take it from there.

[+ friendofsheila]

On 6/14/2026 at 10:53 PM, moonlight said:

He already had your number and didn't do anything with it. He knows you'd be interested. 

I liked this answer so much I made it really really really big.

[+ friendofsheila]

On 6/15/2026 at 8:00 AM, Minneapolis said:

Thanks for everyone's advice.  I'll stop by this weekend and see where the conversation goes.  

whataver you decide to try, good luck 

[+ purplekow]

Any follow up of this?  Curious if you got a no, a yes or a maybe. 

[+ friendofsheila]

4 hours ago, purplekow said:

Any follow up of this?  Curious if you got a no, a yes or a maybe. 

lots of times these threads we never hear the follow up.  

[Becket]

I would most certainly ask him. What do you have to lose? What's the worst he could say? No? You could handle that couldn't you. Go for it!!!

BTW more guys than I ever thought possible are attracted to older guys.

Edited Friday at 01:58 AM by Becket

[Minneapolis]

Sorry guys, I just couldn't.  It's obvious he's flirting for the tips and he's a nice enough guy.  It would never turn into anything romantic and honestly, I wouldn't want it to.  I would just like to have a one nighter and that's it.  I've only been back a couple of times.  He still remembers me and when I gave him the $20 for the drink, he caressed my hand a bit and later blew me a kiss as I left.  It definitely gave me a rush!

I know he's into girls.  He takes girls numbers all the time and tells me he's hooked up with a couple. He use to wear sexy clothes--no shirt, shorts and one time a jock strap--but now its a button down shirt and jeans.  He worked his way up to the best bar to get tips, so I thinks he's coasting a little.   Maybe I'll get the courage one day.  I did ask him what he does besides bartend, and this is all he does.  Two nights a week.  Sometimes 3, but that's it.  So tips are very important.  

I'm actually trying to not go there as much.  I tend to drink too much and I'm focusing more on my health.  It's good exercise to walk there and back, but again, I tend to drink too much when I go so I'm cutting way back.  The 90's aren't what they use to be.  It's still a "gay" bar, but loosely. And I'm not the age demographic, so I feel a little self conscious.  

If and when I do get the courage to appropriately breach the subject, I will report back. I don't want it to be awkward for him either, so I always try to think if I was in his position, how would this feel.  

Thanks for all the advice.  

[Aamir]

30 minutes ago, Minneapolis said:

Sorry guys, I just couldn't.  It's obvious he's flirting for the tips and he's a nice enough guy.  It would never turn into anything romantic and honestly, I wouldn't want it to.  I would just like to have a one nighter and that's it.  I've only been back a couple of times.  He still remembers me and when I gave him the $20 for the drink, he caressed my hand a bit and later blew me a kiss as I left.  It definitely gave me a rush!

I know he's into girls.  He takes girls numbers all the time and tells me he's hooked up with a couple. He use to wear sexy clothes--no shirt, shorts and one time a jock strap--but now its a button down shirt and jeans.  He worked his way up to the best bar to get tips, so I thinks he's coasting a little.   Maybe I'll get the courage one day.  I did ask him what he does besides bartend, and this is all he does.  Two nights a week.  Sometimes 3, but that's it.  So tips are very important.  

I'm actually trying to not go there as much.  I tend to drink too much and I'm focusing more on my health.  It's good exercise to walk there and back, but again, I tend to drink too much when I go so I'm cutting way back.  The 90's aren't what they use to be.  It's still a "gay" bar, but loosely. And I'm not the age demographic, so I feel a little self conscious.  

If and when I do get the courage to appropriately breach the subject, I will report back. I don't want it to be awkward for him either, so I always try to think if I was in his position, how would this feel.  

Thanks for all the advice.  

You sound like a really sweet thoughtful tender guy. As you know some older gay men can be so jaded and defensive, so defeated by a still deeply scary homophobic world,  that they just aren't fun to hang out with.  You seem different.  If you want up to 52 gorgeous twinks in the next 52 weeks,  you'd find love with one or more of them I'm sure of it. Sure 40+ might say no,  but oh well,  do you really want 40 lovers? I heard you when you said you prefer one nighters,  but love is nice at our age too. Good luck sexy!!

[ACluelessGent]

What are you talking about? I want the good stuff your are taking 😅

[+ friendofsheila]

7 hours ago, Minneapolis said:

 when I gave him the $20 for the drink, he caressed my hand a bit and later blew me a kiss as I left.  

Wow straight guys are really crosssing lines to get tips!

[marylander1940]

For bartenders and anyone else making a living out of tips flirting with customers is a good policy!

[BSR]

On 6/15/2026 at 5:49 AM, Minneapolis said:

I tip well—usually $20 for a couple drinks, and sometimes another $20 on the way out. Not outrageous, but definitely above average.

While you’re not leaving C-notes, don’t downplay your generosity.  I’m guessing very few customers tip as well as you do, so it makes sense that your handsome bartender would go above and beyond to be nice in return.

I wouldn’t even invite him out for coffee.  Asking about anything (way) beyond coffee is a huge “Hell No!”  Enjoy it for what it is:  a fun, harmless flirtation with a gorgeous guy.