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I am confused. I deliver to this business on a semi regular bases. There is this young woman there that is half my age who always goes out of her way to greet and talk with me. We have done the eye contact thing, me checking her out, and as far as I can tell vice a versa. She seems so sweet, but I am confused why she would be even egging me on, If that is even the case. Maybe she is just a very nice person. I of course find her very attractive. Been out of the game quite a while now, so was looking for any advise/thoughts worth getting.      

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Thank you for your response/acknowledgement. I am in my late 50s, I would guess she is in her late 20s early 30s . You are spot on , should I take a shot? How do I do it tactfully. Also how to deal with the fallout if it blossoms. Family and friends may not understand. Seems very strange looking for advice now!   

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There is no way to do this tactfully. You will look like a creep and put someone else in a very tough situation, resenting her job. Friendly does not mean let's go for drinks when you are 30 years her senior and she is forced to interact with you because she needs to pay the bills.

Try dating outside of work and don't hit on or make inappropriate comments to anyone you deal with professionally. 

Edited by Rose Mosse
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What do you mean by "checking her out"? Looking at her body?

Maybe she talks to you because she's a friendly person.

Let's say you ask her out and she says no. Would that make your job awkward?  Would you feel embarrassed? 

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18 hours ago, Rose Mosse said:

There is no way to do this tactfully. You will look like a creep and put someone else in a very tough situation, resenting her job. Friendly does not mean let's go for drinks when you are 30 years her senior and she is forced to interact with you because she needs to pay the bills.

Try dating outside of work and don't hit on or make inappropriate comments to anyone you deal with professionally. 

Thanks for your advice. That was why I asked the question. 

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11 hours ago, boltnrun said:

What do you mean by "checking her out"? Looking at her body?

Maybe she talks to you because she's a friendly person.

Let's say you ask her out and she says no. Would that make your job awkward?  Would you feel embarrassed? 

Yes checking her out meant looking at all of her, not just her body. As I already stated she just may be a friendly person, that was part of the reason  asking for advice, and thank you for yours!

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Chat her up some more and see if it is a shallow conversation or goes deeper than just friendly talk.

It isn't our place to decide for her if she wants to date a guy almost twice her age so if you choose to take a shot and she turns you down make sure you are just as friendly and talkative the next time you see her.

  When I was 46 and just starting dating after my divorce I was doing a promotional thing at a wine walk for a charity event I was involved in.  This very young woman came by my station once and then circled back, sat down right next to me and said "I really like older men"  She asked so we exchanged numbers and we went out twice.  I was flattered that a beautiful woman half my age was interested in me but in the end I was not interested in her the person.  I didn't even and kiss her though she leaned in a few times.  Moral of the story; I let my ego do my thinking.  We had fun and she was really cute and nice but kind of a mess and she drank way to much.  I don't regret going out with her or not getting physical.  

  I guess what I am saying is think it through and know what you want before you take a shot.  She may be super friendly to everyone or she may want to have some fun with an older guy. 

The coffee idea is a pretty safe bet.  Daytime, simple and quick.

Lost

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It doesn't have to be creepy or confusing. You might want to ask for input from women as well if you need more outside opinion.

A lot of young people (especially women) tend to be stuck in the service industries which means they're customer or client facing. It might be confusing to you because she's got great customer service skills. A woman who makes the first move and circles you is letting you know she is interested. This woman, on the other hand, appears to be doing her job. 

When I was a lot younger I was stuck with a 60-65 coworker who kept hovering over me, making (the same) jokes, he would be there first thing in the morning when I arrived at work under the pretense of doing something near my desk, make an effort to always chat with me when there was no one else around in the office and made inappropriate comments about my dress, my weekend, make inquiries as to my personal life. I began to go out of my way to avoid this person and it ate up time in my day when I could have been working. It certainly was creepy.

As a young(er) woman, I made excuses that he was just friendly or I had to do my job or it was part of the job to get hit on by older males or have to interact in very inappropriate ways just to keep my job. If I was uncomfortable or I said anything to anyone about it, for a time I thought this would compromise being employed. Who would listen to me? He had been with the company for far longer and it was his word against mine. This guy was very persistent.

You are seeing her as an option. The receiving end is very different. My suggestion is to keep things as respectful as possible even if you do ask her out for coffee (keep it simple, clean and like you're ripping off a bandaid) and consider your ages because there are some gaps that are just not realistic. Be real with yourself and what you're looking for in a partner overall.

If she says no to the coffee, don't approach her again and keep your conversations civil and respectful. 

 

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21 hours ago, lostandhurt said:

Chat her up some more and see if it is a shallow conversation or goes deeper than just friendly talk.

It isn't our place to decide for her if she wants to date a guy almost twice her age so if you choose to take a shot and she turns you down make sure you are just as friendly and talkative the next time you see her.

  When I was 46 and just starting dating after my divorce I was doing a promotional thing at a wine walk for a charity event I was involved in.  This very young woman came by my station once and then circled back, sat down right next to me and said "I really like older men"  She asked so we exchanged numbers and we went out twice.  I was flattered that a beautiful woman half my age was interested in me but in the end I was not interested in her the person.  I didn't even and kiss her though she leaned in a few times.  Moral of the story; I let my ego do my thinking.  We had fun and she was really cute and nice but kind of a mess and she drank way to much.  I don't regret going out with her or not getting physical.  

  I guess what I am saying is think it through and know what you want before you take a shot.  She may be super friendly to everyone or she may want to have some fun with an older guy. 

The coffee idea is a pretty safe bet.  Daytime, simple and quick.

Lost

 

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10 hours ago, Rose Mosse said:

It doesn't have to be creepy or confusing. You might want to ask for input from women as well if you need more outside opinion.

A lot of young people (especially women) tend to be stuck in the service industries which means they're customer or client facing. It might be confusing to you because she's got great customer service skills. A woman who makes the first move and circles you is letting you know she is interested. This woman, on the other hand, appears to be doing her job. 

When I was a lot younger I was stuck with a 60-65 coworker who kept hovering over me, making (the same) jokes, he would be there first thing in the morning when I arrived at work under the pretense of doing something near my desk, make an effort to always chat with me when there was no one else around in the office and made inappropriate comments about my dress, my weekend, make inquiries as to my personal life. I began to go out of my way to avoid this person and it ate up time in my day when I could have been working. It certainly was creepy.

As a young(er) woman, I made excuses that he was just friendly or I had to do my job or it was part of the job to get hit on by older males or have to interact in very inappropriate ways just to keep my job. If I was uncomfortable or I said anything to anyone about it, for a time I thought this would compromise being employed. Who would listen to me? He had been with the company for far longer and it was his word against mine. This guy was very persistent.

You are seeing her as an option. The receiving end is very different. My suggestion is to keep things as respectful as possible even if you do ask her out for coffee (keep it simple, clean and like you're ripping off a bandaid) and consider your ages because there are some gaps that are just not realistic. Be real with yourself and what you're looking for in a partner overall.

If she says no to the coffee, don't approach her again and keep your conversations civil and respectful. 

 

 

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Thank you for your continued advise. I totally understand your concerns. I would never be like that. And if I was to be rejected or if things didn't work out I don't believe that would cause me to be any different towards her. After all I get along with my Ex just fine.   

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Superdave,

I gave your approach a little thought and came up with an idea.  The next time she is talkative with you say this:

"You are really great to talk to and so pretty, if I was a little younger I would ask you for your number"

This throws your true interest out there and opens the door for her.  If she is interested then she can reply:

"Don't let a few years of age difference stop you"  or something along those lines and if she isn't interested she will say "Ohhhh, you are so sweet"   This approach will not be creepy or ruin the rapport you have with her.

Let us know how it goes and good luck

Lost

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17 hours ago, lostandhurt said:

If she is interested then she can reply: "Don't let a few years of age difference stop you"  or something along those lines and if she isn't interested she will say "Ohhhh, you are so sweet"   This approach will not be creepy or ruin the rapport you have with her.

Yep. People in customer or vendor facing positions have been taught that these relationships are important. Some go a bit overboard in catering to these relationships in the hope that good feedback will reach their bosses.

I don't say this to discourage, but rather to remind you that these relationships ARE important, and there's nothing to be confused about in that regard.

If you want to float such a comment as suggested by Lost, Pay Attention to the response. If it's not overtly encouraging, then hang it up and get back to business. 

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On 4/8/2021 at 9:25 PM, lostandhurt said:

Superdave,

I gave your approach a little thought and came up with an idea.  The next time she is talkative with you say this:

"You are really great to talk to and so pretty, if I was a little younger I would ask you for your number"

This throws your true interest out there and opens the door for her.  If she is interested then she can reply:

"Don't let a few years of age difference stop you"  or something along those lines and if she isn't interested she will say "Ohhhh, you are so sweet"   This approach will not be creepy or ruin the rapport you have with her.

Let us know how it goes and good luck

Lost

That is a clever way to approach this . I will give some variation of that a try. You have been very helpful, Thanks.

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If you're already wondering about what friends and family would say, I'm assuming your goal is to have a long term girlfriend, and you're not thinking fling. In that case, the articles I've read with various studies have been that age gap relationships of 20 years or more end in a 95 percent divorce rate. It would be wise to think of if you really want to pursue someone who is in a totally different stage than you because it does present major problems. I'm assuming you're even close to 28 to 30 years older, so she will be retiring decades later than you. While you're home and retired, maybe wanting to travel and do daily excursions with a companion in the retirement years you've worked so hard for, she'll be toiling away at work another 20 to 30 years.

And yes, if circles in both camps raise eyebrows or express concerns over the relationship, even if none of their business, it does incur stress in a relationship.

I, for one, have had to often take care of elderly parents when needed besides working full time and overtime. I remember thinking how happy I was not to have a husband their age, because frankly I couldn't handle taking care of his elderly needs when I already have my hands full with my own parents. I look forward to my spouse and I aging at the same pace, enjoying similar life stages, and not dealing with the issues that come along with age gap relationships.

Either she's just friendly, maybe likes male attention (I used to work in a building where a woman was a people person, dressed for attention, and had many men thinking they had a shot with her when they didn't), or she does find you attractive. If she's too young and dumb to think of what dating you would end up entailing if it spelled forever, at least you as the older person with life experience should have considered.

Just my opinion of course, but it's your life and you can take those risks if you choose. When social distancing is no longer an issue, I recommend Meetup.com activities for singles in your age group. I briefly tried that and enjoyed it, but ended up meeting my husband on OLD.

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