Asking your barista/bartender/server out, and how to deal with unknown ages?

[Unhappy_Nerd]

So, I guess I have two points I'd like to pass by the group-mind:

 

1. What is the general consensus on men approaching women in their workplace?

 

2. How to proceed when you don't know someone's age?

 

 

I'm recently divorced after 18 years of marriage, and honestly I was never really good at reading women. My dating skills are...dated. Last time I asked someone out was basically in high school.

 

There's a barista that I *think* might be interested - she's been super friendly, knows my name, and greets me by name when I come in the Starbucks. I've been something of a regular the past few months. We've engaged in polite & friendly banter - talking about each other's tattoos, and such. But just surface level chatter while she was working on my coffee.

 

I'm super hesitant to make a pass at her at work, but I have no other connections with her. I could potentially find her on Facebook and try to message her on that platform, but I'm not sure how creepy that would be either.

 

Other issues:

I have no idea how old she is, but if I had to guess I'd say about 26-27, judging strictly by appearance...I could be very wrong though. A decade or so age gap wouldn't bother me, but I don't want to come off as a creep if she's a lot younger than that; e.g. 21 or 22.

 

Additionally, I appear a lot younger than I actually am. People usually think I'm 30ish. I don't look or act my age. I think she'd be surprised to learn I'm 38...most people are.

[O'Malley]

It sounds like typical interactions a server would have with a regular, and she's being paid to be a captive, albeit friendly, audience....it's easy to mistake that for personal interest. If you still are interested in asking her out, I'd have more conversations with her, see if you can steer the subject towards events that you could meet up at. You can also give her your contact info but be nonchalant about it and give her space if she's not interested.

[Unhappy_Nerd]

It sounds like typical interactions a server would have with a regular' date=' and she's being paid to be a captive, albeit friendly, audience....it's easy to mistake that for personal interest. [/quote']

 

Which is exactly why I'm super hesitant. I suppose the question should have fewer personal circumstances...

 

So I'll rephrase it a bit:

 

If you're a regular at a bar/coffee shop/restaurant is it a faux pas to ask out your bartender/barista/server?

 

I know they deal with sexual harassment already, and don't want to be one of the people adding to the problem.

Edited July 10, 2018 by Unhappy_Nerd

[lurker74]

Which is exactly why I'm super hesitant. I suppose the question should have fewer personal circumstances...

 

So I'll rephrase it a bit:

 

If you're a regular at a bar/coffee shop/restaurant is it a faux pas to ask out your bartender/barista/server?

 

I know they deal with sexual harassment already, and don't want to be one of the people adding to the problem.

 

It is not a faux pas. I've gone out with a bartender and a waitress that I met on the job. But as said earlier, don't mistake the job performance of being friendly with interest. Look for the cues...dilated eyes, touching of hair, looking at you when you are pointing at something else and talking.

 

But at the end of the day, you just have to ask. Be completely normal about it. DO NOT say, "I Totally understand if you don't want to..." Instead, just come out and say, "Hey, would you be interested in grabbing a non-coffee drink with me sometime this weekend...?"

 

Be clear as to your intent and the time frame (i.e. don't say "sometime"). And if she says she has a boyfriend, smile genuinely and say, of course you do...lucky guy...see you tomorrow...take your coffee and leave (in other words, don't ask until you have your coffee so that you don't have to stand there awkwardly waiting for it).

 

Good luck and report back!

[d0nnivain]

It's not a faux pas to ask out somebody that you as a customer met while they were at work in a service oriented field.

 

However you have to have a thick skin to do it & you have to be able to brush it off like no big deal if you get rejected. You can't get all weird, or else you have to find a new place.

 

 

I'd open with something like "How does your BF feel about you being nice to strange men like me every day?" If she says that he's OK with it, you know she has a BF & you stop dreaming about asking her anything. If she gives you a sharp answer you know she doesn't fancy you & is telling you not to ask. If she giggles & smiles, then you know that she's interested. The next day you ask a Q like where does a barista go for a good cup of coffee? Finally you ask her what time she gets off, which is probably like 3 pm. while you still have another 2-3 hours of work to do & you try to figure out how to ask her out for after your work.

[Noproblem]

Before you ask her out,

 

talk about your favorite 90's shows or bands.

 

if she knows some of them, you might be able to know her age.

 

If she for example said, oh I don't know any of them,

 

you proceed by saying, oh so you are 2000's kid

 

she might correct you telling you she is 25 or something

 

or she might not

 

But yeah try to engage in a conversation about things that only your generation and the second generation know!

 

If she turned out to be in an age range that works for you!

 

Ask her out, what the harm right?

 

If no, you change the cafe!

If yes, you go out!

If it worked out fine, you don't change the cafe

If you broke up, you change the cafe again!

[alphamale]

don't ask women out who are being paid to be nice to you

[Unhappy_Nerd]

Before you ask her out,

talk about your favorite 90's shows or bands.

if she knows some of them, you might be able to know her age.

If she for example said, oh I don't know any of them,

you proceed by saying, oh so you are 2000's kid

she might correct you telling you she is 25 or something

or she might not

 

But yeah try to engage in a conversation about things that only your generation and the second generation know!

If she turned out to be in an age range that works for you!

 

Not a bad idea. I hadn't tried steering the convo towards 80's and 90's era pop culture. That would be a good way to get a feel for her age. Thanks for the suggestion.

 

Starbucks is always so busy that we rarely get to exchange more than a few words and a smile.

[d0nnivain]

Starbucks is always so busy that we rarely get to exchange more than a few words and a smile.

 

Is there a way you can get there during a lull so you & she have a few minutes to chat?

[Unhappy_Nerd]

Is there a way you can get there during a lull so you & she have a few minutes to chat?

 

Maybe...I typically stop by in the morning on weekdays. I have an hour drive to work, and swing by the coffee shop midway. Usually take 10 min to have a cuppa there, and then continue my drive. I might be able to swing by a bit later in the day if I'm taking a half day for some reason.

[d0nnivain]

I might be able to swing by a bit later in the day if I'm taking a half day for some reason.

 

You are going to have to if you want to ask her out. If the place is packed & she's swamped you asking her out will be annoying because of bad timing. Even if she likes you she will say no because it's more expedient & she won't want to give the next guy in line ideas.

[rightondude]

Go at lunch. The Starbucks near me is not busy at lunch and usually starts to get slammed again around 4:00. Ask her: "Hey, what do you like to do for fun when you're not here having fun?" If she responds with anything of substance, I think you have a shot. Ask right then and there, say, "that's cool. Would you wanna grab a drink with me sometime after work?" If she says yes, get her number. Then say you gotta go, you just stopped in for a quick jolt before (some big meeting or something). Then call her and set up detaiils. Don't text her, call her. Lemme know how it goes.

[basil67]

Not a bad idea. I hadn't tried steering the convo towards 80's and 90's era pop culture. That would be a good way to get a feel for her age. Thanks for the suggestion.

 

Cue the response "Oh yeah, my dad used to like that"

[mortensorchid]

don't ask women out who are being paid to be nice to you

 

^This. It's like trying to ask out the student body president. They are not nice to you because they are actually interested in you, it's because they are casting a general popularity blanket over everyone so that they are generally known and liked by all. Plus her employer might not like it if she accepts a phone number from a customer. Think of her position.

[jay1983]

This is one of those hings were you just have to ask.

 

Bartenders (smart ones) don't talk about their boyfriends and may flirt a little. They make more money.like that Lol

[rightondude]

^This. It's like trying to ask out the student body president. They are not nice to you because they are actually interested in you, it's because they are casting a general popularity blanket over everyone so that they are generally known and liked by all. Plus her employer might not like it if she accepts a phone number from a customer. Think of her position.

 

I am the last person to want to make a situation uncomfortable for anyone, but I have for sure worked in retail/sales and would have been just fine with certain customers flirting or asking me out.

 

Of course coming from a dude, it's like yeah, duh, but I have to imagine it's OK with the ladies depending on who is doing the asking. The trick is, be hot!

[snowboy91]

Once upon a time this would be something I just wouldn't do. The barista/bartender is there to be friendly to everyone. If they weren't, the business wouldn't survive.

 

But, if they know you on a personal level, ie. you've talked to them lots over the course of many months and you know stuff about them (and they know you), then there is a chance it could work. Be really casual about it, always keep in mind that they probably aren't attracted to you. But hey, if you can be friends with a cool barista/bartender, that's still a win

[basil67]

I'm curious as to why you're interested in someone so much younger than you.

 

Looking younger than you are means nothing. And acting younger than you are signals immaturity. And if you are immature, she will grow out of you as she gets older. I'm not trying to be mean, just pointing out the obvious pitfalls and hopefully prodding some reflection on your part.

[JuneL]

Try asking her about her work hours. For example, you can ask how her weekend went, and add “Or did you have to work over the weekend?” Then go at a time you can have a longer conversation. Who knows, she might mention her bf or other activities, and you can go from there. I also think it’s a great idea to build some rapport first, so there won’t be any awkwardness in case she turns you down (it’s like asking a colleague out). But I’m sure there’re plenty of Starbucks locations on your way to work, in case you have to change coffee place

[JuneL]

I'm curious as to why you're interested in someone so much younger than you.

 

Looking younger than you are means nothing. And acting younger than you are signals immaturity. And if you are immature, she will grow out of you as she gets older. I'm not trying to be mean, just pointing out the obvious pitfalls and hopefully prodding some reflection on your part.

 

Assuming the barista is 26-27, my cousin and his wife have the same age difference. They’ve been happily married with two adorable kids now. As long as the girl is an adult, who are we to judge?

 

Also, I think when a divorced guys start dating, they tend to play the field and try to have some fun time. It’s not surprising that they tend to go for girls much younger at this stage.

Edited July 11, 2018 by JuneL

[Unhappy_Nerd]

I'm curious as to why you're interested in someone so much younger than you.

 

Looking younger than you are means nothing. And acting younger than you are signals immaturity. And if you are immature, she will grow out of you as she gets older. I'm not trying to be mean, just pointing out the obvious pitfalls and hopefully prodding some reflection on your part.

 

 

I tend to get a long better with people half my age, tbh. Most people my age are focused on raising families, and rarely share my interests anyway. Plus most women my age have a kid or three in tow, and I'm just not interested in that.

 

And yes, you probably would consider me immature. I don't have kids (don't want any, and I had a vasectomy when I was 20), I'm a nerdy gamer geek, I watch a ton of anime, read sci-fi & fantasy, love to go to nerd conventions and renn faires, I'm a metalhead who goes out to live music venues, and the only sports that I participate in are martial arts related (HEMA/historical fencing). My interested align much better with people about 10 years younger than I am.

 

That being said, I "adult" just fine. I'm a senior accountant at an insurance company, with my CPA license. Most of my laundry even ends up in the right laundry basket.

[alphamale]

That being said, I "adult" just fine. I'm a senior accountant at an insurance company, with my CPA license. Most of my laundry even ends up in the right laundry basket.

 

so you're a CPA, you must be making some serious coin. buy a Mercedes or Corvette convertible. Chicks love hot cars.

[Unhappy_Nerd]

so you're a CPA, you must be making some serious coin. buy a Mercedes or Corvette convertible. Chicks love hot cars.

 

Dude, I wouldn't touch a woman who was attracted to me for my car with a 10 foot pole.

 

I'm looking for a specific type: Metalheads, Goths, & Nerds. Women who don't give a crap what normal society cares about. Women with ink, piercings, and unique hair.

 

Any woman that mentions a mainstream religion, sportsball, country music, or their vehicle is right out. Mundanes and Normals need not apply.

 

 

And maybe the above explains a bit better why I'm attracted to my barista?

Edited July 11, 2018 by Unhappy_Nerd

[Doost]

You have a good job so just be confident and ask her out damned the consequences. “Would you be interested in getting coffee sometime?” “I have a bf and my work is coffee.” Seriously what’s the worst that can happen you get fired from your fancy job, put in prison and killed via a prison rape? I think not. Just go for it and don’t overthink it. Play it off like a joke if she rejects you. Say “not!”

[d0nnivain]

Unhappy Nerd

 

If your barrista is as far off the mainstream beaten path as you think, she probably has the thick skin to deal with unwanted attraction from customers. If she doesn't want to date you, she'll have no problem telling you because she dances to the beat of her own drummer & is comfy in her own skin. Similarly, if she's interested, she will accept your offer happily.

 

The key remains finding a time to ask her out that is not super busy. And for you to be chill & not weird or awkward if she declines.