Dating advice?

GravitySucks

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So DGF has been gone for six months now and I'm getting a bit lonely. Friends and family have been wonderful, but there's nothing like the company of a good woman.

I went online and was just about to delete the account when a woman contacted me and we made a date to have coffee. It went well ( going hiking and dinner tomorrow) but things got uncomfortable when the What Do You Do subject came up. At first I could sense she thought unemployed bum, so I tried to explain that I don't have to or want to work, but then I felt like I was bragging, then worse thought I was opening myself up way too much. How do you explain your situation to new people?

Another issue I can see is most women my age are working full time. DGF was in the underground economy so time off was no problem. It was also an uneven relationship monetarily - not that I minded. I'm off to travel for the next few months. I don't know any women that can take off like that other than the unemployed or much older. How do you find companions in the same boat? I don't want to date ten years younger or ten years older.

What's a boy to do?
 
I ended up with a teacher, so she at least had summers off. But the rest of the year, I would occasionally take trips by myself. She is retired now with a good pension, also thanks to being a teacher. Before DW, I dated a number of women that appeared to be just above water or getting support from their parents.
 
... things got uncomfortable when the What Do You Do subject came up. At first I could sense she thought unemployed bum, so I tried to explain that I don't have to or want to work, but then I felt like I was bragging, then worse thought I was opening myself up way too much. How do you explain your situation to new people?

"I'm in asset management for a private client. I'm very fortunate in that I can do it from home or wherever." :)
 
"I'm in asset management for a private client. I'm very fortunate in that I can do it from home or wherever." :)
That sounds like something an unemployed bum would say to justify being unemployed. Just sayin.
 
I told all the women that I was retired. None of them had a problem with that truthful answer.

If someone has a problem with the truth you don't want to hang with them anyway.
 
It is what it is. And some of us are very proud of our unemployed bum status. :D
I understand, but most people below a certain age around 62-65 are not retired and have to work and cannot relate to people who are voluntarily retired and financially secure...it just does not compute. Someone in the dating market who comes across someone who does not work is statistically more justified to assume that the person is a bum who is not financially secure, as opposed to the very rare person who participates on this board.
 
Some time after my late wife died I went online......met some great women, but for whatever reasons none of them stuck......met DW on line 14 years ago......always was up front with all of them, never mentioned dollar values, and I was still living in the 5th wheel at the time....(since we'd been fulltime Rving before the cancer diagnosis).....didn't want any "But I thought...." down the road with any prospects.
 
It is what it is. And some of us are very proud of our unemployed bum status. :D



I've had days when a bum wouldn't take my money. "We don't take from each other"

Really though unemployed bum doesn't seem to play well with the ladies. No matter how good I smell.
 
I understand, but most people below a certain age around 62-65 are not retired and have to work and cannot relate to people who are voluntarily retired and financially secure...it just does not compute. Someone in the dating market who comes across someone who does not work is statistically more justified to assume that the person is a bum who is not financially secure, as opposed to the very rare person who participates on this board.

What do you advise the OP to say when the question comes up?
 
Then you really don't need a story. Partly depends on where you live. Many government workers, plenty corporate pensioners, and in a tech hub plenty of ERs are always around.

Also, what is wrong with 10 or 15 years younger?

Ha
 
Really though unemployed bum doesn't seem to play well with the ladies. No matter how good I smell.
Of course not. Out of 100 unemployed men in their 50's, I would guess that 90 of them are involuntarily unemployed or not financially secure, or both, and yet most of them will not truthfully tell a prospective date "I'm broke and I have no prospects"...they will come up with some song and dance to make them seem more attractive. So you can't blame women for being careful and skeptical in that environment because it's hard for her to determine if you are being truthful or if you are just another BS artist trying to justify being a bum.
 
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When I started dating I was 59. Been with current girlfriend 2 years, getting married next year.

Did Our Time and Match, but found current girlfriend at the city dog park (fellow canine lover) the old fashioned way. See girl in person, chat a bit, ask out to lunch.
 
58 isn't that young to say that you're retired. I would grill you about how you managed to pull that off :) but I think a lot of women wouldn't give it much thought until several dates on.
 
What is wrong with "I used to ..., but now I'm retired ...." ?
 
OP - I would say I'm retired. It's great if she thinks you are poor and still wants to see you.
If she asks how you manage to live, you could say you get a pension of sorts which is enough. Certainly no need to reveal the actual amount of $$$, or sources that funds your "pension of sorts"
 
Maybe it's just the way I grew up, in a house of angry, ignorant, ineffectual drunks, but if somebody isn't all that "in" to me I find it easy and better, to just walk away. I cannot change anyone's mind any easier than they can change mine. Like the basis of the Buddhist philosophy paraphrased as: "Stop going through Life wanting so many things and you'll be happier"

I once heard a little "Life's Lesson" expressed in a movie called "Killdozer." (Yes, I'm the kind of person who notices these things)

Travel light and travel alone. Anything else you get is gravy. It's all good.
 
I am about your age (though taken!) so maybe my thoughts have value. First of all, fifty-eight is not that young - many people in my line of work (Federal govt) retire at 55, and not all take second jobs. They tend to be frugal people who have saved, invested, and have nice 401Ks.

Even if you were younger, I wouldn't assume you are any kind of bum, if you live in a nice place and seem not to be in need. I would consider how you support yourself to be entirely your business...it's not like we're getting married. I would, of course, search your name to see if anything evil pops up (would also help to reveal if you have given me a fake name). I'd expect you to search my name, too.

That said, I would be interested in how you occupy your time....are you writing a book? Going on a 2-month trip? Tending a conservatory of gorgeous plants? (all of which would be OK by me).

Finally, I would wait to see how you treat me and other people. That matters more than anything else.

Good luck!

Amethyst

So DGF has been gone for six months now and I'm getting a bit lonely. Friends and family have been wonderful, but there's nothing like the company of a good woman.

I went online and was just about to delete the account when a woman contacted me and we made a date to have coffee. It went well ( going hiking and dinner tomorrow) but things got uncomfortable when the What Do You Do subject came up. At first I could sense she thought unemployed bum, so I tried to explain that I don't have to or want to work, but then I felt like I was bragging, then worse thought I was opening myself up way too much. How do you explain your situation to new people?

Another issue I can see is most women my age are working full time. DGF was in the underground economy so time off was no problem. It was also an uneven relationship monetarily - not that I minded. I'm off to travel for the next few months. I don't know any women that can take off like that other than the unemployed or much older. How do you find companions in the same boat? I don't want to date ten years younger or ten years older.

What's a boy to do?
 
I'm certainly not going to be dishonest about what I do, but I could see the wheels spinning on ER = Unemployed Bum at coffee. And I really worry about gold diggers, so saying "I'm rich, I do what I want" isn't an option (or true.... Not the do what I want part, the I'm rich part HA)
 
I don't mind telling people that I'm retired, it's no brag, just fact. I did have a funny incident last week while filling out a form needing a name of employer. I wrote the first letter of my old employer, scratched though, and wrote retired. Got a chuckle out of it.
 
GravitySucks - Can you say you're an early-retired "whatever-you-used-to-do-for-a-paycheck"?

omni
 
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