Man flirts with waitress, hands her his number in front of table, friends say 'stop.'

To flirt, or not to flirt, that is the great question facing singles across the world.

Shakespeare wrote plays all about the art of flirting (and the mishaps that go down), countless movies and shows have explored the faux pas of a flirtatious exchange gone wrong, and the discomfort that results from a failed attempt can sting long after. And yet, if you don't shoot your shot, there's no chance at all.

Of course, there are settings where it's appropriate and settings that are far less appropriate, finding the line is the ultimate task.

In a popular post on the AITA subreddit, a man asked if he was wrong for leaving his number for a server.

He wrote:

AITA for leaving my number on the bill?

So, I (26M) went out for dinner last night with a few friends. We were at this pretty nice restaurant and our waitress (F, early 20s) caught my eye as soon as we sat down. I thought she was really cute and had a great sense of style. Her outfit was really unique and just seemed to suit her perfectly.

Anyway, throughout the night, she was really friendly and attentive, and I couldn't help but keep noticing her. After a while, I decided to go for it and compliment her on her outfit. I said something like, 'Hey, I just wanted to say that you look really cute tonight and your outfit is amazing. It suits you so well.' She seemed to take the compliment well, smiling and thanking me.

Later on, as we were finishing up our meal, I decided to write my number on the receipt and leave it for her, just in case she was interested in talking more or even going on a date. When I handed her the receipt, I told her, 'I hope this isn't too forward, but I've really enjoyed talking to you tonight and thought you might like to get in touch if you're interested.'

She took the receipt and thanked me, but I noticed her smile seemed a bit forced this time. I figured maybe she wasn't interested, and that was fine. I didn't want to push her or make her feel uncomfortable. After we left the restaurant, my friends told me that what I did was inappropriate and that I shouldn't have put her on the spot like that at her workplace.

They said it's not okay to hit on service workers who are just trying to do their job. I genuinely didn't mean any harm, and I thought I was being polite and respectful about it.

People were honest with OP about their stance on the situation.

MSTater85 wrote:

'Throughout the night, she was really friendly and attentive.'

It is her JOB to be friendly and attentive.

'She seemed to take the compliment well, smiling and thanking me.'

You are a customer, what's she supposed to do? Throw a drink in your face?

YTA whether you meant to be or not. Please do not go back to apologize or otherwise contact her, you've already put her in a really uncomfortable spot.

Ok_Bookkeeper_3481 wrote:

OMG people still do that?! After all the talk, and the awareness campaigns?

The waitress is at her place of work. Her literal income depends on her being nice to customers - even if they are drooling hounding self-unaware…specimens.

Repeat after me: she doesn’t like you. She is trying to make a living.

YTA , sheesh.

JabbaInBlueJeans wrote:

YTA. This is almost always a bad idea. She's paid to be nice to you. She must get tons of guys hitting on her every day at her job, it's exhausting. If you absolutely had to hit on her, you should have just left your number on the receipt without saying anything directly to her and forcing an awkward encounter. But as a general rule, just leave women alone while they're working.

confusedacrobat wrote:

Soft YTA. As a service worker, I like when people are friendly/flirty. I don’t like when they bring it into the real world by being that forward. A number or note on a bill is welcome, either it’s a compliment or the start of a potentially exciting date. But while she has to respond as your waitress, it’s a little unfair to put her on the spot.

Kateseesu wrote:

YTA. Because someone’s job is to be friendly to you, doesn’t give you the right to talk about her appearance and approach her for a date. Smiling, laughing and being friendly are part of her job. You are not special.

The reason she had a forced smile is because she had to continue to be nice to you, even though you put her on the spot and made her uncomfortable. It probably made her rethink the whole night and wonder where she went wrong in giving you vibes that she would be interested in you.

lyr4527 wrote:

YTA from the moment you made that inappropriate comment about her appearance. She’s a server and is paid to provide you with good service. The fact that she was friendly and attentive does not mean that she’s into you. It’s gross and intrusive to put a service worker in an uncomfortable position by hitting on them while they’re just trying to do their job.

You should never have commented on her appearance, let alone asked her out and left your number. Also, dude…generally speaking, if you start by saying “I hope I’m not being too forward,” that’s a sign to stop immediately and not say what you’re about to say. If you think you’re being forward, you are. Stop.

Clearly, the internet agrees with OP's friends.