How do I let this older guy know I’m interested in going out with him?

[Anonymous]

There’s a regular customer where I waitress. He’s a lot older than me and we talk all the time. I know he’s interested because he always asks for my section and wants to know what days I work and I’ve caught him checking me out. He’s nice and he’s mature and not at all like the usual guys I date. But I’m afraid he might not ask me because of our age difference. He’s in his late 50’s and widowed and I’m in my early 20’s.

we have great chats, and I’ve tried to be obvious and flirt with him. My skirts get shorter, my tops get lower cut and he tips more. But that’s it. How can I send a more clear that I like him without seeming like a total slut?

[Pyrofox]

If he's older by like 30 years you maybe don't want to do the flirt thing. Instead wear something that makes you seem proud to be a mature woman with a slight hint of flirty. And I'm pretty sure he would take the bait in full. He's not going to make a move if you look too young. Ya gotta dress the part so he doesn't feel like he's going to get called like your grandpa...

[Pyrofox]

I guess my best tip is dress like a 40 something year old hot milf is I guess another way to put it. And watch him be like unable to stop staring 💙

[Pyrofox]

Fair warning about that idea it might work too well. 🙄

[Asker]

Thank you. I work at a bar so a little bit sexy helps with tips. I don’t know if dressing like a grandma is going to help much with that. But I can try to dress more mature for days I’m sure he will be there. Sometimes I wonder why he even talks to me. He’s so much more worldly and smart than me. But it’s always the highlight of my day.

[Pyrofox]

It's not grandma ma'am it means just a bit dated. Dress what his age would find sexy.

[OlderAndWiser]

Start taling to him about other restaurants, mention a restaurant that you recently discovered that you are "just dying to try," but you hate eating alone. If he doesn't get that hint, you have no chance!

[slatyb]

He's not asking you because he assumes you would not be interested due to the age difference. You are going to have to ask him yourself. Say "I'm off on , would you like to get some lunch/dinner/whatever" or "I get off at..., want to get a drink / dinner / whatever is appropriate."

[Guido]

Just tell him you really enjoy his company and the conversations you have. Give him your number and tell him that if he would like to get together outside of your work then your interested and leave it up to him.
A lot of older guys may be attracted to a younger woman but won't make the first move because it can come off as being a creepy old man preying on a young woman.
Good luck and you will probably make his day.

[Asker]

Are you sure that wouldn’t seem too forward. Or like I’m looking to jump into bed with him? I don’t know why but guys always seem to assume that I’m a party girl, and maybe I used to be but I’m not anymore

[Guido]

Just keep it casual and do not make any sexual comments. Keep it about the conversation and spending time talking and younshould be fine. It may develop into more but you set the pace. Be in control of what you want.

[zagor]

Sounds like he likes you but figures you wouldn't be interested.

I'm afraid I can't think of anything offhand.

[Ram-man]

Just ask him for a coffee or drink. Don’t over think it.

[IHateBeingaMan]

is he over a decade older than you?

[Asker]

He is probably thirty years older than me. But he’s in good shape and very interesting. He makes me laugh and I want to just get the chance to talk with him outside of work. Maybe he will think I’m boring or silly. But the highlight of my day is when he comes in.

[Anonymous]

Damn girl. You give a fella hope.

[Anonymous]

You go girl.

[deshazoj2]

Tell him

[Anonymous]

Looks like a troll