Dating advice?

[Souschef]

I was blessed to find someone who loved to travel and was retired. When we were first seeing each other, she got a fortune cookie that read, "You will set foot on many strange lands". At that point she did not even have a passport
She still has that fortune in her passport case, 42 countries and 10 years later.
As far as finances, at the time I was still wor%%ing, as I had to have my late wife's medical covered. After she passed away, I still continued for lack of anything else to do.
Then I met DW, who was financially struggling in the aftermath of her husband's passing. She was very up front about her situation, but I hung back for obvious reasons. When we got really serious, I let her look at my balance sheet, just to be aboveboard about everything.
She then revealed her finances to me. The reason she held back was that her older son warned her not to tell anyone what she had, which I thought was reasonable advice.

 

[Amethyst]

Curious, what is with this big fear of moochers/gold diggers? How could they even get that far with us? It seems like there would be very early clues...never picking up a check, for instance. And then there would have to be a talk.

 

[imokurok]

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?

Thankfully I'm not in this situation, but I've thought about "the explanation" after I FIRE.
"What do you do?"
"I'm a private investor."
"Do you have a lot of money?"
"I do okay."

I don't want their money, and not looking to hang out with anyone that wants mine.

 

[haha]

Curious, what is with this big fear of moochers/gold diggers? How could they even get that far with us? It seems like there would be very early clues...never picking up a check, for instance. And then there would have to be a talk.

I don't really see a problem either. If you are dating for love, ok, you don't want to be played. But if you balance the overall books ( money, emotion,sex, fun, etc.) monthly or so, who cares? Don't worry about small amounts of money, if you are a guy you will seem hopelessly tight-fisted, and it does cost her more than little to look good, which most of us men do appreciate. Don't forget that most pastimes are not free, so why should dating be free? Personally, I am not interested in the eating out of meals, or rides on the Ferris wheel. And I wish I could get a lifetime pass to avoid the annual or semiannual zoo trips. These things would be terminally boring were it not that one is doing them with an attractive woman. A risk is that if you fall in love, then BF or GF gets into trouble you feel crappy if you don't help, but can also feel played if you do depending on circumstances and how things turn out.

I would never give a P & L to a date or a GF. If she really wants to know, let her hire a PI. If you are a man, stay in shape, keep your nails clean, wear gloves if you work on cars, shave and shower, and if you can, learn to dance. Oh, also keep your apartment or home neat.

Save your financial status for your banker.


Ha

 

[Souschef]

I would never give a P & L to a date or a GF. If she really wants to know, let her hire a PI. If you are a man, stay in shape, keep your nails clean, wear gloves if you work on cars, shave and shower, and if you can, learn to dance. Oh, also keep your apartment or home neat.
Save your financial status for your banker.
Ha

I agree if it is a date or GF, but when it becomes a serious relationship there has to be some idea of what each of you has.

 

[GravitySucks]

Really more an I don't want to be seen as a potential moocher. As for scammers and gold diggers ask any of our LEO members if they've ever heard of people getting taken for thousands over the Internet. Not too worried, but don't want to be taken for a meal ticket either.

Fun Fact - Talking with DGFs friend about her online dating. She called Tinder her free dinner app. Act a little interested and guys would take her to all the places she could never afford.

I'm a bit old fashioned, so I will be intending on paying for the first few dates. I'm not a cheapskate. However, It was nice to have the young lady offer to pay for her half of the check and to follow up with a can I at least get the tip when I refused.

 

[Nemo2]

I'm a bit old fashioned, so I will be intending on paying for the first few dates.

How about initially meeting for a coffee or a walk or a museum or somesuch?

Me, I corresponded by e-mail with women before meeting them; wanted to get their measure, (at least partially), beforehand.

DW & I, even once the first levels of a potential relationship were underway, walked and talked and walked and talked and......

I found out who she was, and likewise she determined who I was.

 

[ivinsfan]

Well... I like me, too, but I think we all know that 100% honesty doesn't typically work well in the dating game. Obviously you want to avoid outright duplicity, but I see absolutely no harm in saying that you're some sort of consultant, or (as someone else suggested) a private wealth manager. The last one is very strictly true, and the first one is vague enough not to be a lie. IMHO, complete and total honesty will not get you very far in the dating world, but YMMV. Consider this hypothetical first date banter:

She: "So what do you do for a living?"
You: "I was an (X) for many years, but I'm retired now."
She: "Wow, you're retired? But you're only 58! Are you rich or something?"
You:

So this was an honest unfiltered answer,isn't that what you are looking for..give a very short answer that says you aren't rich.you saved and planned for a long time to live in a way you value. She will either ask intelligent questions and show interest,or say I'd like that but my car just got repoed and I just bought my 500th pair of shoes..why play games

 

[GravitySucks]

Yes Nemo. Tomorrow I am picking a date up and going to a beautiful State Park. We both enjoy hiking. Followed up with a dinner at a restaurant where I've never eaten before.
I want someone to share what I enjoy and have no problem springing for dinners and concert or movie tickets.

 

[athena53]

Curious, what is with this big fear of moochers/gold diggers? How could they even get that far with us? It seems like there would be very early clues...never picking up a check, for instance. And then there would have to be a talk.

I'm more concerned about the real pros, who seek out wealthy widows. They drive nice cars, pick up the check at fancy restaurants, send them flowers the next day... and when they've reeled them in, they tell them about this can't fail investment opportunity in their business. Sure, I'd dump the guy at that point but by then it's a big emotional hit because you trusted someone and they weren't worthy of it.

And yes, I HAVE watched too many episodes of American Greed. In general, though, I'm very cautious about displaying any indications of high net worth. My everyday wear is so casual people probably think my Rolex is fake.

 

[Nemo2]

I've never forgotten a Jules Feiffer cartoon that I must've seen some fifty years ago.......two vertical strips, approximately six panels each.

On the left side, progressing downwards, there's a guy saying how he took his date to a fancy restaurant on their first meeting; his expenditure increases on every date, and on the last panel, feeling the pinch, he suggests they go to a movie....she dumps him.

On the other side, the guy says they went for a walk on the first date, window shopping on the next, etc, etc, in the same vein. Last panel he suggests they go to a movie...and remarks to the effect that "Was she ever happy!"

 

[GravitySucks]

And yes, I HAVE watched too many episodes of American Greed.D

My wonderful friend had to remind me of the Criminal Minds episode where the serial killer picked her victims from a dating web site before I went out on my first OK Cupid date.

 

[growing_older]

I have had interesting results with online dating. When I wrote a profile that included being almost retired and generally having good financial means, I got lots and lots of attention from many women, but didn't find any of them that I was interested in. When I wrote a much more low key profile, not quite saying I was an unemployed bum but pretty close, generally understating my financial position, I got a lot less attention and found it harder to get women to reply back - but those that did were much more interesting and compatible people.

I've heard that online dating can be a numbers game, but it's important to remember that all numbers don't matter, just the likelihood of finding the kind of person that you would actually like.

 

[FlaGator]

OP- we could be twin sons from different mothers

From what I've seen from your posts about your relationship history, I think you've been very thoughtful about your experiences and are moving forward carefully. You have seen the downside of being committed to someone, yet persist. Tells me you believe it's all worth it. I agree

After the first failed relationship after my wife of 30 years died, I was concerned about a few things:

1. Being a target for those in less comfortable circumstances
2. Wondering if I was "damaged goods" after being married as long as I was was and yet still having two kids to get launched. Who would want to get involved with a guy in his mid-late 50's with those responsibilities?

The question of my means of support is likely always there, but I stopped worrying about it. I'm retired with enough to live the life I want, and that's how I explain it when it comes up. No need to get into how that happened (pensions, savings, etc.). Probably still leaves questions unanswered, but I figure those can be dealt with later, when the time is right.

As to gold diggers, I think that is entirely within our control. This is one I now realize I worried about too much. IMO, they are easier to spot than they think they are. No one can get more of your money than you are willing to give them.

I stick to a reasonable budget for socializing (dinners mostly, and wine after a walk on the beach). I don't get lavish with gifts. Last thing I bought her was a $15 adjustable arm to get her shower head to a more usable place. Rebuilt a closet before that. All things that made her life easier, and she appreciated. Don't get me started on what I did for the one before her.....Learned a lot from that experience

As to "damaged goods", I've stopped worrying about that one too. I can't change my circumstances, and everyone I've met in the dating process has things I would once have found less than ideal. Now figure as long as nothing is being hidden or shaded, we each can decide how well the situation fits with our respective life goals.

Best wishes finding the lady worthy of your loyalty. Don't settle, the right one is out there

 

[Amethyst]

Again, I am thinking of myself as a young woman (haven't dated since my late 20's), but I imagine the same sort of things would please me now as did back then. I did not think about lavish gifts, and I wouldn't now. I was perfectly willing to go Dutch, only nobody would let me I suppose the fate of an older woman is that now the men expect you to pay. Oh well!

What pleased me the most was someone doing simple maintenance on my car, helping paint the house I had somehow managed to buy (this also allowed my future husband to display how good he looked in tight jeans), excitedly planning a small trip that we were both paying for. The shower head thingy would have pleased me no end. As you say: Things that make your life easier, and more fun.

Nowadays I can hire someone to do all of the above, but I would think an experienced older man could still think of ways to make a woman's life easier.

And as you say, we are all "damaged" in somebody's eyes (we have a lot of miles and have taken depreciation along the way) so there is no sense worrying about it. Just play up your good points and try to see everyone else's.

No one can get more of your money than you are willing to give them.

I stick to a reasonable budget for socializing (dinners mostly, and wine after a walk on the beach). I don't get lavish with gifts. Last thing I bought her was a $15 adjustable arm to get her shower head to a more usable place. Rebuilt a closet before that. All things that made her life easier, and she appreciated. Don't get me started on what I did for the one before her.....Learned a lot from that experience

As to "damaged goods", I've stopped worrying about that one too. I can't change my circumstances, and everyone I've met in the dating process has things I would once have found less than ideal. Now figure as long as nothing is being hidden or shaded, we each can decide how well the situation fits with our respective life goals.

Best wishes finding the lady worthy of your loyalty. Don't settle, the right one is out there

 

[donheff]

58? Tell them you retired early. What's the big deal. I ERd at 56 and most people were envious, they didn't view me as a bum.

 

[Nemo2]

58? Tell them you retired early. What's the big deal. I ERd at 56 and most people were envious, they didn't view me as a bum.

I'm 75 this month, quit working at 46.......I was a bum before that, and I'm a bum now.

 

[athena53]

I have had interesting results with online dating. When I wrote a profile that included being almost retired and generally having good financial means, I got lots and lots of attention from many women, but didn't find any of them that I was interested in. When I wrote a much more low key profile, not quite saying I was an unemployed bum but pretty close, generally understating my financial position, I got a lot less attention and found it harder to get women to reply back - but those that did were much more interesting and compatible people.

The first paragraph is sad but believable. I've considered saying that I was capable of paying my own way in transatlantic Business Class and wanted someone who could do the same. I could see that attracting guys like my first husband, who dressed well and talked a good game, but had a boatload of credit card debt and no savings.

 

[Totoro]

37 (like me), or 58 (like you), the problem is essentially the same: finding a compatible partner. For that you need to:

• Know who you want
• Know what that person wants
• And get that point across

That's the generic, and useless part. These days there are so many flexible and non-flexible arrangements in lifestyle, work etc .. that frankly I wouldn't be with anyone who can't understand that a traditional work model is not the only option out there. Also, you are 58? Not working is almost the norm in that age category.



In my situation, in the periods that I was/am a bum I have said that I am considering my options after a few years of hard work, that I work as an independent professional in irregular intervals, or that I am a part-time investment advisor for a small family office. All of which were true. In online profiles I tend to overplay and reword a bit to distinguish myself from the 'entrepreneur'-types who actually indeed are walking life-destroyers and failed haphazard no-career types.



Most of them are geared to signal that I am not worried about my financial future, but also don't communicate I am a target to siphon off of. In later conversations the details can come up.


Chances are your current lady of interest gauges you correctly as well: Don't underestimate the things you say and non-verbal communication. Your life story shows up in many ways. I wouldn't worry too much about getting the wording exactly right once you are in the real world.


Online profiles indeed can be tricky, but easily experimented with.

 

[imokurok]

I've never forgotten a Jules Feiffer cartoon that I must've seen some fifty years ago.......two vertical strips, approximately six panels each.



On the left side, progressing downwards, there's a guy saying how he took his date to a fancy restaurant on their first meeting; his expenditure increases on every date, and on the last panel, feeling the pinch, he suggests they go to a movie....she dumps him.



On the other side, the guy says they went for a walk on the first date, window shopping on the next, etc, etc, in the same vein. Last panel he suggests they go to a movie...and remarks to the effect that "Was she ever happy!"

Happiness = Expectations/Reality

 

[Sojourner]

Fun Fact - Talking with DGFs friend about her online dating. She called Tinder her free dinner app. Act a little interested and guys would take her to all the places she could never afford.

I dated a woman who said this exact thing on our first date! Talk about honesty. We didn't meet on Tinder, but she told me how much she liked the app and how using it had enabled her to "experience the finer things in the city for free". Needless to say, when the check came, she didn't reach for it.

I think this is an unfortunate and widespread side effect of online dating services. It had led to many women treating dating sort of like channel surfing. I read an article about this recently that explained the psychology of it all very convincingly. It's just so easy for any reasonably presentable woman to find a date at a moment's notice, that when they actually do go on dates they are constantly evaluating and scrutinizing the guy in comparison to the next "virtual" one who's out there who might be a little better looking, a little taller, a little funnier, a little richer, etc. So they end up churning through a stream of guys who could be very good matches over the long term, in search of the "perfect" match. Very dispiriting for those of us non-George Clooney types.

 

[omni550]

Early-on in my online dating experience, as I was driving to another meet-and-greet, I had this thought....

When we were high school/college age, we were all like "new cars" in the dealer's showroom. Typically were meeting/dating/marrying the young people from our neighborhoods and schools who were basically "blank slates" like ourselves. In other words, we were all shiny, brand new vehicles.

Later in life, we are all like "used cars".... quite unique...some are low mileage, some are high mileage, some have had multiple owners, some have rust, some have dents and dings, some have a lot of bondo/repairs...and some have trunks overflowing with baggage or are towing a trailer (full of who-knows-what).

So dating now (for both men and women) is sort of like looking for a good used car....without access to a CarFax report.

omni

 

[Amethyst]

Unfortunately, I can definitely see this happening with younger women. I don't think it is going to be too much of an issue with older ones, though. We know Prince Charming isn't actually around the corner, and if he does, he has nose hair.

I dated a woman who said this exact thing on our first date! Talk about honesty. We didn't meet on Tinder, but she told me how much she liked the app and how using it had enabled her to "experience the finer things in the city for free". Needless to say, when the check came, she didn't reach for it.

I think this is an unfortunate and widespread side effect of online dating services. It had led to many women treating dating sort of like channel surfing. I read an article about this recently that explained the psychology of it all very convincingly. It's just so easy for any reasonably presentable woman to find a date at a moment's notice, that when they actually do go on dates they are constantly evaluating and scrutinizing the guy in comparison to the next "virtual" one who's out there who might be a little better looking, a little taller, a little funnier, a little richer, etc. So they end up churning through a stream of guys who could be very good matches over the long term, in search of the "perfect" match. Very dispiriting for those of us non-George Clooney types.

 

[GravitySucks]

Well, guess this one saw unemployed bum from the first meeting as she just texted to postpone the second date.

 

[scrabbler1]

Back in my dating days, I had a policy for first-date blind-dates. We would meet for coffee and/or a snack in a low-pressure setting which took less time than a longer dinner-date, for example. The women always went along with this, as they welcomed a similar setting. It also didn't cost as much, so I never had any reservations about paying the whole check. (If she insisted on paying her own way, fine.)


This was also a good method to weed out any gold-diggers who were in it only for a free meal. Thankfully, this happened only once. One woman insisted on a full dinner-date. I balked at that, telling her that if things went well on our smaller first-date, I would be happy to have a second date that way. She became hostile, calling me a cheapskate and said lots of nasty things to me. I told her I was glad to learn now that she saw me only as a free meal. We went our separate ways.


But several years later, she happened to reply to some ad I had posted on line. She don't know we had corresponded years earlier. While it was tempting to do something to get even with her, maybe stand her up for a date, I also wondered if she had reformed and changed her attitude. So I first told her that we had chatted before on line and that she had been mean to me. After inquiring further, I told her what had happened years earlier and asked her if she still felt the same way about insisting on a full dinner on a first date. She said she had and that ended our chat. But she wasn't hostile and berating this time.


I have almost always paid for my dates over the years. This is because I made more money than the women did. In many cases, the women were unemployed and lived with their parents (even well into their 30s). I was happy if they offered to pay the tip on a dinner, at least it was a sign they weren't in it for the free meal.