Does this older man like me? If so, how do I get to make the next move?

[Thatoneoverthinker]

Hi everyone! I met this man (looks like in his mid 40s or mid 50s) about a year ago at an event, (keep in mind this event has only men in the organization... I know, it is odd but only men wanted to sign up)! That night that we first met, he shook hands and had a picture taken of us but as the person was fiddling, trying to get their camera to work, he mentioned something interesting and said "this is the longest I've held somebody's hand since my ex-wife" and laughed, I laughed along it and just blushed. That night I spoke to other guests and I'm assuming he overheard that I received a job offer and so the night for me ended and I left home without saying goodbye to him.


Time passes and we meet again (the same amount of guys I saw from the year prior), about a couple of weeks ago we met again and when I entered the room, he was the first man I spotted. Minutes later he comes up to me and asks about how I've been and whatnot, we were able to catch up but what really caught me off guard was when he mentioned the job offer and wanted to know more about that. It surprised me that such a man would remember what happened that night and wanted to know more. So, we spoke and then sat at tables, I went and sat first and he came up to me and sat down across from me saying "now I'm sitting with the cool kid" and laughed, I laughed too. We were speaking about how COVID has really affected the community harshly, then I spoke about how it affected me and anyone in education currently, and he understood and listened and agreed with all of it. We spoke about that then I asked about wanting to get to know him better, so he gave me his story of how he got in the organization and I listened the whole time. He then spoke about me to people that night about how amazing I was and how far I've gotten as a young woman and how far I'll even get from my passions. When I had to say goodbye, he winked at me and said "I'll see you soon!"

So, what do y'all think? If so, how do I ask him out?

[ChrisMaster69]

Sounds promising.

do you have anything in common you talked about, if so that would be an ideal date.

failing that how close distance wise are you to each other, restaurant’s, type of food do you both like?

basically contact him and just say ‘do you fancy doing xyz’

if it’s email, text, mobile, etc.

just say you really enjoyed his company last few times, but it would be nice without all the other distractions.

just be open, honest, make it clear it’s just a chat etc.

you set the rules and he follows them.

[Thatoneoverthinker]

Thanks for the help! I am a huge politico and I'm sure he would be too, so maybe that could be a talk for our date, but what ways do you think I should ask him in person without sounding all nervous or creepy.

[ChrisMaster69]

@Thatoneoverthinker just be confident, don’t over think it lol.

Really just write it out if needs be.

However you normally communicate is fine.

Just be concise and say exactly what you want and expect.

Choosing venue can be fun, link that to a question on say ‘what restaurant do you think is best for quiet discussions on xyz and why’

This then has him thinking of where he likes to go, it gives you an insite,

Then when he says the name you have a choice,

You can come back with

1. So did you book a table for two (or for us).
2. I am really happy you eventually asked me out, I dropped enough hints (depends on how you get on).
3. Okay, do you fancy booking xx date at xx time for us and we can discuss xyz.

[ChrisMaster69]

@Thatoneoverthinker thanks most appreciated

[Thatoneoverthinker]

No problem! In fact, thank you for helping me... sucks that the internet doesn't have a lot of advice on how to flirt with older men in comparison to dating advice for men my age. :/

[ChrisMaster69]

@Thatoneoverthinker as an older guy (40) that flirts a lot, I tend to know what I want.

My main thing is the other person being talkative and not an interrogation just to get simple chatting going lol.

Good luck hope it really works out for you, lucky guy.

[Thatoneoverthinker]

Yeah, I tend to get nervous around him but he eases the nervousness by throwing a couple of jokes here and there. I'm currently having doubts, but from what was shown on here, and coming from your perspective, do you think he is interested in me or just throwing it as a friendly thing?

[ChrisMaster69]

@Thatoneoverthinker it is really hard to tell how exactly someone thinks of you.

The main thing is though, you can try flirting back and making it subtly obvious that you would like taking things further, or not do anything and think about the ‘what if I had…’.

He may be nervous he comes over as the predatory one being older, or that you will simply laugh your tits off that someone his age could remotely interest a younger girl.

Being burned is a real thing for guys, it’s getting past that and removing his vulnerability,

[Thatoneoverthinker]

Ah, I see... so subtle flirting or conversation starters could be a way to go. What about just looking at him and smiling? How does that feel necessarily when a girl looks at you and smiles at you?

[ChrisMaster69]

@Thatoneoverthinker if a girl looks at me and smiles, I will smile back, however you then go through the dance of flirting to find out if it was a random smile or if she was signalling you.

A nod of the head with the smile, makes it more pointed to the person you are targeting,

Sort of indicating you saw them smile and are saying hello back.

Depending on distance etc you talk or carry on with body stuff lol.

With me, I would likely indicate I wanted to come over and then simply walk over and chat to you,

But it varies hugely between people

[Thatoneoverthinker]

Oh, I see. But considering his age, I should approach him first. Also, at this event, it's just a bunch of older men, so how should I talk to him without people creating assumptions of him and I and possibly making him stray away because of that? Like last time, I was the only female at the event they hosted and all older men were gawking at me, so when he walked up to me, everyone was looking at us.

[ChrisMaster69]

Find some place quieter, away from the circling sharks.

Indicate where you want to meet, ask even people if there is a separate bar and contact him to meet there, so you have his email, or mobile number?

If so do it ahead of the event and simply organise it.

[slatyb]

Do, you know how to contact him? Just invite him to dinner, and suggest a time and place. If possible, pick something you can afford to pay for, although he will probably insist on paying. Let him.

He won’t ask you because of the age difference. Older gentlemen don’t hit on very young women. Good luck.

[Thatoneoverthinker]

I did get his number last year, but I'm not really sure how to start a good conversation on text. The gathering is happening again next Wednesday so I want to wait until after then so we can talk and it gives me a reason to text him so we can catch up. Do you think that is best or what should I do?

[slatyb]

If you are going to see him again on Wednesday, invite him somewhere after the event? Or to dinner on Friday or Saturday. Lucky man.

[Thatoneoverthinker]

That sounds good! The only problem is, is that we have really only met twice and the last time we met, we actually had a long conversation. So, I kind of want to get to know him some more before I play any moves so I know for sure he is interested. What do you think about this? (Also, yeah he should be pretty lucky to have a young woman gawking over him)

[slatyb]

"So, I kind of want to get to know him some more..." Yeah, that's the point of getting together over a meal. But it could be anything. You could just ask him if he wants to take a walk. If you were fearless, what would you say to him?

[Thatoneoverthinker]

That's true, I just am worried about being rejected. But I will take your advice, I think too much of it :)

[slatyb]

You might just ask "Would you consider dating me?" If he declines, life will go on. He'll still be a friend. If you want anything to happen, you are going to have to ask. Most men his age will not make advances on a very young woman for fear that it would be quite unwelcome.

[Thatoneoverthinker]

That is true, but from all those subtle signs, do you think that there is interest on his end?

[slatyb]

Seems like he's crushing on you. Anyway the only way to get what you want is to ask for it.