"suspicious" Older Man Asked Me Out

Enyo

Enyo

Well-Known Member
So, on Friday I'm chillin' the the lobby of a nearby building that has a cafe inside. This older (late 50's-ish) man makes small talk with me and he's really charming. I noticed his Panerai and told him I studied in Florence. He smiled and told me it was one of his favorite cities and started doing the "old man telling stories", but it was cool because I love to travel. When he asked me out, I wanted to laugh, but he was so dang charming that I said yes. He gave me his business card with his information and told me to let him know when I was available.

So, I go back to my desk and Google his name. It turns out he owns a successful business, owns two homes here in Hawaii, and one in Seattle. He probably makes really good money, so I'm wondering what this old wealthy guy wants with me. I'm nice looking, but not all that. I was going to allow him to take me to coffee anyway, but now I'm suspicious and have yet to message him. I know I'm overthinking, but that's just how I am.

Opinions? Thoughts?

And, yes, I'll probably go eventually and give you ladies a report (be it bad or good).
 
Enyo said:
So, on Friday I'm chillin' the the lobby of a nearby building that has a cafe inside. This older (late 50's-ish) man makes small talk with me and he's really charming. I noticed his Panerai and told him I studied in Florence. He smiled and told me it was one of his favorite cities and started doing the "old man telling stories", but it was cool because I love to travel. When he asked me out, I wanted to laugh, but he was so dang charming that I said yes. He gave me his business card with his information and told me to let him know when I was available.

So, I go back to my desk and Google his name. It turns out he owns a successful business, owns two homes here in Hawaii, and one in Seattle. He probably makes really good money, so I'm wondering what this old wealthy guy wants with me. I'm nice looking, but not all that. I was going to allow him to take me to coffee anyway, but now I'm suspicious and have yet to message him. I know I'm overthinking, but that's just how I am.

Opinions? Thoughts?

And, yes, I'll probably go eventually and give you ladies a report (be it bad or good).
Click to expand...
First, why wouldn't he want to date you? You are beautiful and that's all the reason anyone needs. Go have fun and report back on your wonderful date.

Second, why is he suspicious? He didn't seem creepy or anything from what you divulged.
 
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Ms.Lyons said:
First of, why wouldn't he want to date you? You are beautiful and that's all the reason anyone needs. Go have fun and report back on your wonderful date. Second, why is he suspicious? He didn't seem creepy or anything from what you divulged.
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No, he was very respectful. I dunno. I just get a certain kind of "younger" woman in my head when I think of someone dating a financially comfortable older white guy. Really pretty and white. Stereotypes, I know.
 
Enyo said:
Yeah, I'll try. But my history with men is pretty bad, so I'm always guarded. Even more so with this guy.
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Maybe peruse the men don't love women like you thread. You could read the book before your date. I'm not sure what your issues are but hey it's a start.

However, I think you'll do great if you just don't think too much into it. He is just a man. You are a women he's interested in and should be showing you who he is. He obviously liked whatever you did when you weren't looking at him as potential love interest. Keep that up as you don't know him to be all in your head about him just yet. Guards are good to have up until he proves who he is is what you are looking for.

I know it's easier said then done but just have fun and remember he's there to entertain you!
 
hopeful said:
Maybe your intuition is telling you to be careful? Or that something is off about him?
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Well, my history is bad in terms of men taking me for granted or being downright flaky. There was a guy I met on eHarmony or one of those websites who had a really crazy schedule. He was always working and could never find time for me. We talk on the phone for over a month. But one of his old friends from the military called him on Thursday night and he was able to see them Friday morning. Needless to say I never talked to him agai after I found that out. Take that type of situation, multiply it by eight years and there you go.
 
Enyo said:
Well, my history is bad in terms of men taking me for granted or being downright flaky. There was a guy I met on eHarmony or one of those websites who had a really crazy schedule. He was always working and could never find time for me. We talk on the phone for over a month. But one of his old friends from the military called him on Thursday night and he was able to see them Friday morning. Needless to say I never talked to him agai after I found that out. Take that type of situation, multiply it by eight years and there you go.
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I have read nothing suspicious in your OP. Just how old are you, if you don't mind me asking?
The only thing I read suspicious or disconcerting is that you are at risk of sabotaging because of disappointing past experiences.

Perhaps your issue is that this date came about so easy?
No games, just normal conversation and a mutual interest.
If we live in the world that we all claim we should; an older White guy meeting a younger Black woman with shared interest should proceed this way with no worry's over racial baggage.

For some reason we get it in our head that it has to be hard or some kind of cat and mouse.
I think it's wonderful, and incredibly natural that he asked you out.
No manufactured and forced eDate to stress over; just pure organic woman meets man and a connection is made.

I think you should be fine. Take normal precautions and enjoy.
That's if you really want to meet this guy and continue enjoying each others company?
 
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Enyo said:
Well, my history is bad in terms of men taking me for granted or being downright flaky. There was a guy I met on eHarmony or one of those websites who had a really crazy schedule. He was always working and could never find time for me. We talk on the phone for over a month. But one of his old friends from the military called him on Thursday night and he was able to see them Friday morning. Needless to say I never talked to him agai after I found that out. Take that type of situation, multiply it by eight years and there you go.
Click to expand...

I understand. I see two things at play. You don't seem in touch with how you felt with him. You know, if your instincts were telling you something about him. It's not what he said necessarily, it's about your female intuition. Secondly, there are a lot of time wasters out there. As women we have to learn to speak up and move on quickly if a person doesn't make us a priority. That guy didn't deserve an entire month of your time.
 
hopeful said:
I understand. I see two things at play. You don't seem in touch with how you felt with him. You know, if your instincts were telling you something about him. It's not what he said necessarily, it's about your female intuition. Secondly, there are a lot of time wasters out there. As women we have to learn to speak up and move on quickly if a person doesn't make us a priority. That guy didn't deserve an entire month of your time.
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Yeah, but anyone who's familiar with my situation knows I've been struggling with finding a stable relationship for quite a while. It's easy to say to move on quickly, but if you don't have many prospects (and I don't), there isn't anything to move on to. That's how I ended up in a really weird "not dating but we act like we are" with a guy who I wasn't attracted to and got on my nerves. I only stayed around him because I didn't have any other options. Still don't, to be honest.
 
CurlyMoo said:
I have read nothing suspicious in your OP? Just how old are you, if you don't mind me asking?
The only thing I read suspicious or disconcerting is that you are at risk of sabotaging because of disappointing past experiences.

Perhaps your issue is that this date came about so easy?
No games, just normal conversation and a mutual interest.
If we live in the world that we all claim we should; an older White guy meeting a younger Black woman with shared interest should proceed this way with no worry's over racial baggage.

For some reason we get it in our head that it has to be hard or some kind of cat and mouse.
I think it's wonderful, and incredibly natural that he asked you out.
No manufactured and forced eDate to stress over; just pure organic woman meets man and a connection is made.

I think you should be fine. Take normal precautions and enjoy.
That's if you really want to meet this guy and continue enjoying each others company?
Click to expand...

I'm 35 and very tired of the frequent disappointment. I dunno. Even talking about all this is making me second guess contacting him.
 
Enyo said:
Yeah, but anyone who's familiar with my situation knows I've been struggling with finding a stable relationship for quite a while. It's easy to say to move on quickly, but if you don't have many prospects (and I don't), there isn't anything to move on to. That's how I ended up in a really weird "not dating but we act like we are" with a guy who I wasn't attracted to and got on my nerves. I only stayed around him because I didn't have any other options. Still don't, to be honest.
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Seeing this makes me question if you are actually attracted to this older guy then.
Are you considering seeing him because you feel he is one of few options or are you are genuinely interested in him?
Like Hopeful said, I don't see anything mentioned about how you felt toward him during the conversation other than suspicion.

Why do you feel you have no options?
 
Enyo said:
I'm 35 and very tired of the frequent disappointment. I dunno. Even talking about all this is making me second guess contacting him.
Click to expand...
Okay, thought you may have been 22 or something.
I know talking about it feels awkward.
But sometimes I think putting things out in the open gives you another perspective as opposed to keeping it in your head.
 
CurlyMoo said:
Seeing this makes me question if you are actually attracted to this older guy then.
Are you considering seeing him because you feel he is one of few options or are you are genuinely interested in him?
Like Hopeful said, I don't see anything mentioned about how you felt toward him during the conversation other than suspicion.

Why do you feel you have no options?
Click to expand...

I want to hear more of his travel stories, but no, I'm not attracted to him. I have very few options. I keep meeting military people who are always being uprooted, much older men like the guy in question, or guys with kids who live with them and I'm not interested in being anyone's stepmother. I posted about this one guy I really liked, but he thought it was okay to bring his 10 year old son on our so-called "dates". :nono: Then there is the fact that I'm bipolar (literally) and many people in general are turned off by that. I take meds and everything, but I still get depression and mania when I'm super-stressed.
 
Enyo said:
I want to hear more of his travel stories, but no, I'm not attracted to him. I have very few options. I keep meeting military people who are always being uprooted, much older men like the guy in question, or guys with kids who live with them and I'm not interested in being anyone's stepmother. I posted about this one guy I really liked, but he thought it was okay to bring his 10 year old son on our so-called "dates". :nono: Then there is the fact that I'm bipolar (literally) and many people in general are turned off by that. I take meds and everything, but I still get depression and mania when I'm super-stressed.
Click to expand...

Okay things are more clear now.
Will have to continue when I return from work.
 
Enyo said:
Yeah, I'll try. But my history with men is pretty bad, so I'm always guarded. Even more so with this guy.
Click to expand...
You'll be fine. The type of rich guy who doesn't want the norm usually likes a challenge (this is coming from someone who used to work for a successful matchmaker). You seem to have stumbled upon out of the box rich guy.

Challenge doesn't mean ridiculously difficult though :lol: but a little guarded is okay. Besides, you are not supposed to just dive in head first. He will respect that anyways. Every woman should guard her feelings in the beginning. Hopefully that doesn't mean you can't be pleasant AND guarded though.

Go have a good time!
 
Enyo said:
I want to hear more of his travel stories, but no, I'm not attracted to him. I have very few options. I keep meeting military people who are always being uprooted, much older men like the guy in question, or guys with kids who live with them and I'm not interested in being anyone's stepmother. I posted about this one guy I really liked, but he thought it was okay to bring his 10 year old son on our so-called "dates". :nono: Then there is the fact that I'm bipolar (literally) and many people in general are turned off by that. I take meds and everything, but I still get depression and mania when I'm super-stressed.
Click to expand...
Uhm...so what are you going on a date for? You want to go out on a date to hear stories? That sounds like a grab a coffee thing not a date. He is going to think of you as a potential romantic interest for sure. Just know that.
 
It really hurts my heart to hear you talk about yourself in such an unsure way.
You deserve the best. It's not that serious. Go and have fun. I'm not saying you shouldn't be wary just not for any of the reasons you stated.
He wants to get to know you, Naturally. :)
But the question is is he worth getting to know? that's what you're going to find out on your meeting up.
 
Well, usually older men know what they want in life and he wants you. Altho they can be playas too, mostly they have past that point in their life. Girl go have a sit down with ole head. They can be captivating as they are seasoned and has seen a lot.
 
I was cyber stalking him since I have down time at work and he had an open photo album of him going out, fixing his bike, etc. There is a very pretty dark skinned lady (like, the ebony hued flawless dark skin that makes you want to slap her) on his arm, but they were taken 2-3 years ago. Black don't crack, so I cannot estimate her age, but she looks to be mid 40-ish.

He's taking me wine tasting in a few days. :look:

Edited for spelling
 
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Enyo said:
I was cyber stalking him since I have down town at work and he had an open photo album of him going out, fixing his bike, etc. There is a very pretty dark skinned lady (like, the ebony hued flawless dark skin that makes you want to slap her) on his arm, but they were taking 2-3 years ago. Black don't crack, so I cannot estimate her age, but she looks to be mid 40-ish.

He's taking me wine tasting in a few days. :look:
Click to expand...

Have fun!!
 
Enyo said:
So, I go back to my desk and Google his name. It turns out he owns a successful business, owns two homes here in Hawaii, and one in Seattle. He probably makes really good money, so I'm wondering what this old wealthy guy wants with me. I'm nice looking, but not all that. I was going to allow him to take me to coffee anyway, but now I'm suspicious and have yet to message him. I know I'm overthinking, but that's just how I am.

Opinions? Thoughts?
Click to expand...

If you know that he has two houses, one in Hawaii and Seattle, then I'm sure you researched as to whether he's single and/or has any kids. :laugh: If you got the all clear, then definitely at least go out on one date and see whether there are any sparks. You owe it to yourself to at least try, (and keep us posted).
 
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