How to attract an older guy?

[Anonymous]

I really like this man who is 13 years older than me.

We work at the same company but not with each other anymore.

I’ve always really liked him and we are friends but I don’t know what to do.

[MrCommodore]

You have to flirt with him in a subtle way first, and watch how he reacts and responds.

If he reciprocate the subtle flirting, then flirt in a more obvious manner, the objective here is to detect if he is interested without explicitly revealing your feelings and encourage him to make the first move.

If you work with him a long time and you're both friends, you need to be subtle first. There are ways for you to gauge if he likes you, like asking for his help.

[Asker]

So I think we do subtly flirt with each other sometimes. For example compliments, catch each other looking, touching etc things like that. But this subtle flirting has been going on since January so I’ve maybe got the wrong idea because I like him so much.

I’ve known him for 3 years now. But noticed he became more flirty this year and started acting differently with me. It’s kinda awkward sometimes because I genuinely can’t tell if he’s just being nice or is interested. 🫣

How would you suggest to flirt in a more obvious way? I do ask him for help sometimes.

[MrCommodore]

I probably need more info on how you currently interact with him before I can make decent suggestions on how to flirt in a more obvious way.

However normally to be more obvious I would suggest
- Cheeky/Suggestive text messages, nothing too bad, just emoji that make him wonder. Also privately message him sometimes with something funny that reminds you of him.
- Seek his help with a project (Make one up if necessary) that will require only his help, get more time together.
- Take an interest in his interests outside of work, you don't need to know his interests well, just get him chatting about it.

This is all stuff based on me not knowing or understanding your situation, so obviously some might not work or apply to you both, but that can be adapted.

[Asker]

Hey thanks! I would say we do all of the above already but that’s as good as it gets.

[MrCommodore]

Ok, well if you are doing all of the above already, how is he reacting? Are you both single?

[Asker]

Yes both single and he does all the same things back to me. Although he is sometimes a bit more suggestive. Most of the time we are just friendly then other times he’s more suggestive and very flirty.

[JamesDiaz11]

If he's single, ask him out on a date. If he's 40-50, successful, and good looking, chances are he's got his pick of a lot of women out there. This isn't the time to play games (you're over 30 yourself; so, you're too old for this); so, just ask him and see what happens.

[Asker]

Thanks! Embarrassingly I have never asked a guy out! I’m worried he only sees me as a friend/colleague so I’m unsure how to make it obvious.
I was with my ex for 7 years and before him I was never in a more serious relationship so this is all new to me..
I’m 29 but yeah practically 30 😉

[JamesDiaz11]

I was just guessing based on your anon age range. I get that guys should typically ask the girl out, but just say, "hey, it's been too long since we chatted, since we don't work together anymore. Would you like to go get a drink to catch up?" Simple as that- this could be just a friendly gesture, but from there it's on him to turn this into a date, or just a drink with a friend.

Good luck.

[Berethor]

How hard could it be? men tend to prefer young women by default.

[Anonymous]

Listen... Listen... Look... Most people... Tiptoe their way through life hoping to make it safely to death. You know what to do. Stop playing around. It isn't magic or rocket science. Ask him out.

[Avicenna]

You want him to spend time with you outside of work. So invite him to something you know he'll accept

[Ironic_Method]

"Hey, I like you. Let's go on a date."