Question about asking a man out.

[HopefulFriend]

I'm new here and needing some advice about a situation. My friends have varying opinions on what I should do. It’s gotten to the point that it’s embarrassing to me.

There’s this man that I really like. I’m in my mid-forties and he’s in his late forties, so that makes this situation even sillier. I met this man through work, but we don’t work together. It’s more like he does training for my work every year or so. Because of this I see him maybe once a year or once every two years.

A few years ago, I realized that he is good looking, and I am definitely  interested. I’m not the type to get strong feelings very often for any man. He seemed to be somewhat interested in me too. I’m shy and he’s shy too which makes things challenging.

 When I saw him this year, I flirted with him. I thought he was flirting back, but now I’m not so sure. We talked and he was leaving he said, “take care of yourself.” That felt like a definite good-bye to me. Neither one of us took the opportunity to ask the other one out.

I have asked some of my friends what I should do since I think this man is attractive with a personality that complements mine well.  Some are saying, “He should have stepped up and asked you out. If he was interested, he would ask you out, even though he’s shy.” Other friends are saying things like, “It’s 2023. A woman should be able to ask a man to go out. He probably wants to go out but doesn’t know how to approach the situation.”

I don’t know how much this plays into the situation, but I am divorced with no children. I have been divorced for nearly 10 years and have dated very little in that time. He has never been married with no children. I don’t know much about his personal life. He is a fairly private person.

Part of me wants to call him and ask him out. Another part is terrified of rejection. I’ve never asked a man out before. Usually, they just ask me out.

[Foxhall]

8 minutes ago, HopefulFriend said:

I have been divorced for nearly 10 years and have dated very little in that time. He has never been married with no children. I don’t know much about his personal life. He is a fairly private person.

Potentially you are a good match and if he is shy he may need a little help from the woman,

ask him out and see where it goes.

[Wiseman2]

4 minutes ago, HopefulFriend said:

When I saw him this year, I flirted with him. I thought he was flirting back, but now I’m not so sure. ,  I am divorced with no children. I have been divorced for nearly 10 years and have dated very little in that time. He has never been married with no children. I don’t know much about his personal life. Part of me wants to call him and ask him out. 

Are you friends on social media or connected on LinkedIn? What type of contact information do you have?

You only see him once a year? Since you know nothing about him, I disagree with your friends about calling him out of the blue and asking him out.

He may be in a relationship, may not want to mix business with dating or may simply not be interested. 

Please consider getting a good profile and pics on quality dating apps and start talking to and meeting local interested men. If you hear from him again, great, if not, you're getting on with your life. 

[d0nnivain]

No sane man employed by corporate America as a "trainer" is going to ask out a trainee he met in class.   It's just not going to happen. 

Do you know his relationship status?  You don't want to ask if he's married, exclusively involved or not playing on your team.   

Assuming you can ascertain that he is single, reach out with a pretextual question about the last training.   Then segway into would he like to grab a drink or coffee.  Keep it LIGHT.   If he says yes, great!  If he says no, chalk it up to his loss, move on & NEVER mention it again.   Remember if he declines there may be a myriad of reasons including the situation (trainer / student) that have nothing to do with your value or desirablity.  

[HopefulFriend]

13 minutes ago, Foxhall said:

Potentially you are a good match and if he is shy he may need a little help from the woman,

ask him out and see where it goes.

Thank you for the advice! I have thought about doing that.

[HopefulFriend]

14 minutes ago, Wiseman2 said:

Are you friends on social media or connected on LinkedIn? What type of contact information do you have?

You only see him once a year? Since you know nothing about him, I disagree with your friends about calling him out of the blue and asking him out.

He may be in a relationship, may not want to mix business with dating or may simply not be interested. 

Please consider getting a good profile and pics on quality dating apps and start talking to and meeting local interested men. If you hear from him again, great, if not, you're getting on with your life. 

He has no social media accounts to my knowledge, and I have very few. We have a few mutual friends / acquaintances. I am nervous about calling him out of the blue. He is aware of who I am, but the fact that he may not be interested makes me nervous.

I have given some thought to trying dating apps in the near future. It's something I've never tried before, but I guess something good could come from it.

Thank you responding and the advice!

[HopefulFriend]

9 minutes ago, d0nnivain said:

No sane man employed by corporate America as a "trainer" is going to ask out a trainee he met in class.   It's just not going to happen. 

Do you know his relationship status?  You don't want to ask if he's married, exclusively involved or not playing on your team.   

Assuming you can ascertain that he is single, reach out with a pretextual question about the last training.   Then segway into would he like to grab a drink or coffee.  Keep it LIGHT.   If he says yes, great!  If he says no, chalk it up to his loss, move on & NEVER mention it again.   Remember if he declines there may be a myriad of reasons including the situation (trainer / student) that have nothing to do with your value or desirablity.  

That's good advice. I do know that he is single. That's about the extent of it. I've been trying to convince myself that if he says no it's not a reflection of who I am. It's nice to have validation from someone else about that. 

[Foxhall]

Interesting, I missed that part that he is delivering training,

I have some experience teaching night classes- for sure situations can arise where there is a temptation to get involved further with a learner,

If I were completely single again- I imagine I would view it as my best means of meeting someone.  

 

 

 

[Alpacalia]

Do you know what his interests are? If he enjoys wine (example) get his opinion on an up and coming winery or tasting. This way, you are showing your interest without being too direct. If he's interested, he will likely take the opportunity to ask you out on a date.

You can always play it off as just wanting to get his input on something related to his interests. 😉

[Lotsgoingon]

Call him and ask him out. BTW: what the heck do you mean by saying it was silly to have this romantic spark interest because you were in your 40's. That's just spectacularly foolish to think. Please tell me you do not really believe that. 

Edited December 2, 2023 by Lotsgoingon

[HopefulFriend]

18 minutes ago, Alpacalia said:

Do you know what his interests are? If he enjoys wine (example) get his opinion on an up and coming winery or tasting. This way, you are showing your interest without being too direct. If he's interested, he will likely take the opportunity to ask you out on a date.

You can always play it off as just wanting to get his input on something related to his interests. 😉

That's a great idea! I do know some of the things he likes. I will try to work that into a conversation with him. Hopefully soon!

[HopefulFriend]

19 minutes ago, Lotsgoingon said:

Call him and ask him out. BTW: what the heck do you mean by saying it was silly to have this romantic spark interest because you were in your 40's. That's just spectacularly foolish to think. Please tell me you do not really believe that. 

I don't think it's silly to have a romantic interest in your 40's. Love can happen at any age. I just feel like it's silly that neither one of us has seemed to work up the nerve to ask the other one out. And I know that that's just as much on me as it is him.

[Lotsgoingon]

Oh, I get it. You both are being cautious (maybe the downside of being 40). But go for it! 

Your script is just going to be something like, "I really enjoy talking to you. Don't see you often. I wonder if you'd be interested in doing X?"

Go for it!

[HopefulFriend]

9 minutes ago, Lotsgoingon said:

Oh, I get it. You both are being cautious (maybe the downside of being 40). But go for it! 

Your script is just going to be something like, "I really enjoy talking to you. Don't see you often. I wonder if you'd be interested in doing X?"

Go for it!

That's it! I think I will go for it!

[Alpacalia]

23 minutes ago, HopefulFriend said:

That's it! I think I will go for it!

Why don't you ask him in a group setting since you both have mutual friends? That's what I did once. He turned me down, but then asked me for a one on one date so it ended up working out in the end.

[HopefulFriend]

5 minutes ago, Alpacalia said:

Why don't you ask him in a group setting since you both have mutual friends? That's what I did once. He turned me down, but then asked me for a one on one date so it ended up working out in the end.

That's awesome!

[Alpacalia]

2 minutes ago, HopefulFriend said:

That's awesome!

I guess... lol

[LuckyM]

As a single man, I agree with being cautious, not ask him out or call either. That is not the answer

you want to hear. Nothing wrong both in your forties, but how do you know his age? You know

little about him...and you are transferring your desire for a guy and loneliness, to him.

It is hard to find another reason to get together. You have no idea where he lives, maybe far away.