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Old 03-31-2024, 09:58 AM
 
Location: Forests of Maine
37,443 posts, read 61,352,754 times
Reputation: 30387

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Be honest with him.

1. Tell him that you wish to continue being his client.

2. Tell him that you like him and you are interested in dating him.

You are both adults, tell him what is on your mind and let him respond.
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Old 03-31-2024, 10:23 AM
 
2,953 posts, read 1,637,449 times
Reputation: 7296
How much longer will your business relationship last? Is the service he's providing coming to an end? Or is it ongoing?

I don't agree with not mixing business with pleasure, people meet in all kinds of ways. But it's always a good idea to approach situations like this cautiously and casually.

First order: find out his relationship status.

Then, does he know you're single? If you are, let it be known.

Without knowing anything about your particular situation it's difficult to give specific advice. I think it's best to avoid asking someone "Out" out.
Don't make the first approach a "Date" it puts too much pressure on both people, with the implications of romantic entanglement.

Rather, make it a companionship "it's just lunch" time spent together suggestion.
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Old 03-31-2024, 10:40 AM
 
27 posts, read 9,968 times
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Quote:
Originally Posted by rokuremote View Post
Has he asked if they're real?
No
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Old 03-31-2024, 10:42 AM
 
27 posts, read 9,968 times
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Quote:
Originally Posted by rokuremote View Post
Has he asked if they're real?
No
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Old 03-31-2024, 10:44 AM
 
19,603 posts, read 12,206,783 times
Reputation: 26394
If you are ok with the possibility he might just want one thing, then it doesn't really matter how you go about it.

No, not all guys are like that. This one is not a gentleman scanning your body like that especially in an obvious way. At his age he knows just what he's doing.

Lunch date would probably last about fifteen minutes before he wants to head out to your place. lol.
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Old 03-31-2024, 10:57 AM
 
Location: New England
3,249 posts, read 1,739,106 times
Reputation: 9125
Quote:
Originally Posted by Submariner View Post
Be honest with him.

1. Tell him that you wish to continue being his client.

2. Tell him that you like him and you are interested in dating him.

You are both adults, tell him what is on your mind and let him respond.
What he said. Carpe Diem!
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Old 03-31-2024, 11:45 AM
 
27 posts, read 9,968 times
Reputation: 35
Quote:
Originally Posted by RubyandPearl View Post
How much longer will your business relationship last? Is the service he's providing coming to an end? Or is it ongoing?

I don't agree with not mixing business with pleasure, people meet in all kinds of ways. But it's always a good idea to approach situations like this cautiously and casually.

First order: find out his relationship status.

Then, does he know you're single? If you are, let it be known.

Without knowing anything about your particular situation it's difficult to give specific advice. I think it's best to avoid asking someone "Out" out.
Don't make the first approach a "Date" it puts too much pressure on both people, with the implications of romantic entanglement.

Rather, make it a companionship "it's just lunch" time spent together suggestion.
This is exactly what I will do. (I'll let him suggest it's just lunch but I'll give him an opening maybe)

I will ask if he's single and tell him I am. Pretty sure he is and that he knows I am. But, even though I think it's forward to ask, I will directly ask him. . .
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Old 03-31-2024, 11:48 AM
 
2,953 posts, read 1,637,449 times
Reputation: 7296
Quote:
Originally Posted by Random10 View Post
This is exactly what I will do. (I'll let him suggest it's just lunch but I'll give him an opening maybe)

I will ask if he's single and tell him I am. Pretty sure he is and that he knows I am. But, even though I think it's forward to ask, I will directly ask him. . .
Go for it!

Good luck
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Old 03-31-2024, 11:53 AM
 
27 posts, read 9,968 times
Reputation: 35
Quote:
Originally Posted by tamajane View Post
If you are ok with the possibility he might just want one thing, then it doesn't really matter how you go about it.

No, not all guys are like that. This one is not a gentleman scanning your body like that especially in an obvious way. At his age he knows just what he's doing.

Lunch date would probably last about fifteen minutes before he wants to head out to your place. lol.
I totally agree.

It felt like a bit much, him looking me up and down pausing on my chest. I'm naive though, I thought he wanted to hug me when I left lol. He may have thought he could hug me and kiss me and everything else right then and there! I don't know. I do listen to my instincts though. Besides my fear of rejection, this is why he has to ask.

I'm ok with making a little "progress" by asking him directly if he's single and telling him I am.

I met my husband randomly (divorced but not at all due to his not being a gentleman) and he later told me he figured I'd be easy to have sex with lol. I knew we'd marry from the second I saw him. It's possible men, in general, think I'm easy but they can think what they want.
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Old 03-31-2024, 12:52 PM
 
6,849 posts, read 4,847,655 times
Reputation: 26330
Doesn't matter who leads. Once you've thought through any possible negative ramifications. Maybe in your line of work there wouldn't be any, in which case....go for it.
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