Should I shoot my shot?

[Anonymous]

I have been a regular customer at a local bar/restaurant for a few years now. I am very friendly/familiar with most of the workers there, and it is a nice comfortable place for me to hang as a solo female patron.

One of the shift managers (not a waiter or bartender, not working for tips) has always been very friendly and polite (as he is with everyone), but lately I have noticed an uptick in the attention he gives me - deeper conversations, physical touching (hand on the back, hug/kiss hello/goodbye), flirtatious eye contact from across the room, winking, smiling, asking me to come back the next day, telling me not to leave, even offering to walk me out when I get up to go. It's all been very gentlemanly, and I am definitely not mad at it.

I have always had a soft spot for him, and this increase in attention is definitely fanning those flames. But I also know that it is his job to create a welcome environment, and it makes sense that the longer I am a regular presence, the more comfortable and friendly the staff and I will be. I don't want to be one of those patrons that ruins a comfortable environment by misinterpreting the rapport for interest and putting him on the spot while he is at work...

But I also really want the opportunity to interact with him outside of his workplace, and it is my personality to do so (if he were a fellow patron, I totally would have slipped him my number already). My friends say to just leave it alone and enjoy the situational flirting/banter. But I also hate to think I'm letting something with potential slip away... Thoughts?

[SueShe]

The question here is: What are your intentions? What is your ultimate goal when flirting with him or rather him with you?

Flirting, by definition is:

"a sexual behavior involving spoken or written communication, as well as body language, by one person to another, to suggest interest in a deeper relationship with the other person".

Now, we obviously all know what is meant with a "deeper relationship", right? That simply means getting into the pants of a woman.

His behavior is very unprofessional and he should never let it come that far when interacting with a customer, client or patron.

I would advise against it unless of course, fornicating is what you ultimately want.

[Staximus]

Please join a convent and become a nun and stop insulting people because they want to live a normal life and have romantic relationships and sex like normal people.

[Anonymous]

You already made mention of one of the main reasons: you are very much a regular and it makes sense for him to become more comfortable with you. The other reason I’d say is about the money. I’m sure you tip him well.

[msc545]

That's a very difficult problem. Perhaps it will turn out that some night. You won't have a ride and you'll need a ride home or you'll be in some other situation where you need a bit of outside help externally of the bar and you can recount it to him without directly asking him for the help. Of course, if he offers you can take him up on it. I think it's really essential to me outside the restaurant and bar in some fashion or another in order to have a conversation that doesn't involve the restaurant and the bar. In this way you can avoid being just the difficult patron and become something more if you wish to be.

[msc545]

Thank you for the mho

[bowenw]

Go for it. You have nothing to lose and you'll probably regret it if you don't.

[bowenw]

Thank you for the MHO. 😊
Let us/me know if you get anywhere with him.

[OlderAndWiser]

Go for it, or live the rest of your life looking back, wondering, and probably feeling regrets.

[AviatorTom]

It never hurts to ask. So go for it.

[Bitter_Sweet94]

It sounds like there’s definitely some mutual interest, but the tricky part is the workplace context.

He’s in a position where friendliness is part of the job, so it’s hard to separate professional courtesy from genuine attraction.

A low pressure way to ‘shoot your shot’ could be giving him your number casually something like, ‘Hey, if you ever want to grab a coffee outside work, here’s my number.’

That way, it’s clear you’re interested but doesn’t put him on the spot while he’s working.

You’ll get a sense of his interest without disrupting the environment, and if he responds positively, you have a path forward outside the workplace.

[OneViewpoint]

Shoot your shot. It doesn't have to get weird. You think you're the first or only person ever to misread another person's polite conversation in a hospitality industry job as romantic interest? At worst he'll be flattered but not interested. And he's not gonna let that jeopardize his job. He'll be respectful and kind. So you get some minor embarrassment. You'll live. And that doesn't mean you stop going to that place. Do you have any idea how many people in the hospitality industry get hit on by customers?

Maybe you get closer are friends. Maybe you get a boyfriend. The risk seems low for the potential reward.

[Zionne]

It sounds like you’re picking up on genuine interest, but the tricky part is that he’s in a professional role where friendliness is expected. A safe way to explore this is subtle: engage in slightly more personal conversation, and if the vibe continues to feel mutual, you could suggest meeting outside work in a casual context (like coffee or a group outing) without putting him on the spot. That way, you can gauge his interest while respecting professional boundaries.

[Noredcarpet]

He has to make the move to ask you out properly, I think. If I were you I would do nothing. He's a guy, he knows what to do, no offense. A tip could be if you went outside and he would meet you right outside and see if he take the opportunity then.

[Zack-Bann]

What are you even waiting for?
Sounds beautiful


Go for it.


Honestly if you do it with good energy even if he doesn’t wanna go out with you he’ll be flattered and cordial about it
(And that’s worst case scenario)


More than likely he’ll be delighted

[lightbulb27]

you are 36-45 and have no time to waste. get the job done. if it doesn't work, you are slightly embarrassed. if it does work, you are on the rocket launch pad to somewhere else.

[Staximus]

If somebody's touching you, telling you not to leave, wants to see you the next day, and walking you out, I'd say it's more than just being friendly. Ask him to go do something fun with you or go out to eat at another restaurant. Just do it.

[slatyb]

Invite him to lunch or coffee or a drink at a convenient time.

[Pohjolan]

Well women do all kinds of things short of making a move like suggesting doing something that would include just the two of you so could start with something like that.

[exitseven]

you should go for it but be prepared to fing a new place to hangoiut if it goes sideways

[Anonymous]

Do you base most life decisions at your age on internet stranger advice?

[Massageman]

Old basketball axiom- You miss 100% of the shots you don't take.

[DrPepper12]

Didn't read a word. The answer is ALWAYS yes

[Twalli]

slip him your number. If he contacts you, there's something there. If not, you took your shot.

[robocop666]

start small work your way up. check small body langauge first.

[Anonymous]

That phrase is so low-life and trashy.

[ABC1x1x]

The answer is always yes.

[jazzy34]

Sure, go for it. 😊

[Enginn]

Yes. Always shoot your shot

[Anonymous]

It's your personal choice.

[Ava007]

Yes before someone beats you to it.

[Jmmmfi4]

We only regret the chances we don't take

[LiamJHayden]

Yes.

[khyalove4]

go for it