Asking out a well-known guy on a date

[Dmills]

This might sound crazy, but I’m going to ask anyways.

There’s a guy who is pretty well-known in the city I live in, and he’s the kind of guy I’d love to date and get to know better. He is single and has an occupation which means he is in the media frequently, but he’s close to 40 and has expressed his desire to meet someone and start a family. If he was not well-known, I’d approach him without thinking about it (like if I saw him in a bar), but I am unsure of whether I should ask him out given the circumstances, and if so, how? I know the location of his workplace (it’s public knowledge), but he would have an assistant or someone monitor letters, emails, social media, etc. I see him in person from time to time, but it’s hard to get him alone to ask him out or slip a note with my number. I thought of sending him something with a note and my number, but I’m not sure if that would come across as creepy.

I am personally a low-key person but would have the confidence to ask him out if I got the opportunity to do so in person, but it’s hard when he’s always surrounded by a crowd. I figured the worst that could happen is that I get rejected, which I am willing to accept. 

 

[Kwothe28]

5 minutes ago, Dmills said:

I thought of sending him something with a note and my number, but I’m not sure if that would come across as creepy.

Sorry to say but anything you put as an option comes along as creepy.

You have a celebrity crush. That is fine. I would also like to date Alexandra Daddario. She is married now but you know how those celebrity marriages are lol. Point is that its a fantasy situation. Its not real and therefore attainable. If you can somehow get introduced and talk to him, then maybe you can exchange numbers and make something more of it. Like this its just fan- celebrity crush. 

[Wiseman2]

22 minutes ago, Dmills said:

I see him in person from time to time, but it’s hard to get him alone to ask him out or slip a note with my number.

How do you know him? Are you a fan?

[smackie9]

The only way is to be a part of his social group, his personal life activities, be where he hangs out, etc. Sending him a message won't work, he most likely gets plenty. You are low key, he won't notice you. I suggest you stick to low key guys. 

[SooSad33]

31 minutes ago, Dmills said:

he would have an assistant or someone monitor letters, emails, social media, etc. I see him in person from time to time, but it’s hard to get him alone to ask him out or slip a note with my number. I thought of sending him something with a note and my number, but I’m not sure if that would come across as creepy.

So you really don't know each other at all?  And you doing this, would probably seem to him like another 'fan' trying to reach out?  Yes?

I suggest you try to actually do something like this in person, so he can see who is talking to him.  Not your number & a note, etc. being dropped off at his workplace.

 

[Wiseman2]

5 minutes ago, SooSad33 said:

 And you doing this, would probably seem to him like another 'fan' trying to reach out? 

Agree, it comes across as something a groupie does.

[lostandhurt]

If he is social then figure out where he likes to hang out.

Your best bet is to follow him on social media and comment on his content in a flirty way once in a while, not to often but often enough so he will notice.  If you are his type he will notice.

Interestingly enough I always thought this one newscaster was super cute and seemed really nice but never ever thought about trying to meet her.  Well I do a lot of volunteering and she happened to be covering one of our events (I was a bachelor being auctioned off for a date) and we met.  She brought along her friend along and after talking to them both for some time I realized she was pretty flaky and although she was my kind of pretty she was certainly not my type.  I did hit it off with her friend though...

Moral of the story is: What you see on TV or social media is what they want you to see, the real person underneath my not be someone you want to spend time with.

Lost

 

[boltnrun]

1 hour ago, lostandhurt said:

Moral of the story is: What you see on TV or social media is what they want you to see, the real person underneath my not be someone you want to spend time with.

Lost

Remember, most appearances and performances are scripted. So the way they come across isn't necessarily their true self.

I'm sure you've seen plenty of instances where a much admired public figure ended up being a garbage human in private. For example, I thought Kevin Spacey was a talented actor and I enjoyed his performances in some of my favorite films. But he's actually a terrible person.

[Lambert]

Do you know him? 

I guess you could follow his social media to see where he hangs out and try to meet him.

but what you're asking sounds like it's more than, "I want to ask a guy out"

[Batya33]

7 minutes ago, Lambert said:

Do you know him? 

I guess you could follow his social media to see where he hangs out and try to meet him.

but what you're asking sounds like it's more than, "I want to ask a guy out"

Agree with all the others- ask him out after you meet him in person and have an actual one on one conversation with him.  

[Andrina]

If he's so successful and attractive, at age 40, why hasn't he ever been married or started a family? And just saying so now doesn't mean he means it. He could have been saying what he thought the public would like to hear. He might even hide his sexual preference, as some celebrities do.

Are you really being realistic that dating him would be satisfactory, when he is constantly being surrounded by an entourage?

Sounds like his one-on-one time is limited. 

After I dated someone for a year who worked about 68 hours per week, I never wanted again to date someone who rarely had leisure time.

I just listened to an interview with Reba Mcentire, and she said that there were thousands of women who had better voices than her, but would never be as successful as her because Reba had to give up a normal personal life to achieve the success she's had. She had to miss some holidays, some of her son's special events like hockey games, etc. She said if those women weren't willing to sacrifice a normal family life, they would never be successful in the music world.

How old are you? What's your relationship history been to date?