Meeting Someone at 50 Years Old. Different Than 25

poorboy

Well-known member
Aug 18, 2001
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I've been on three dates with the same woman now. What you're looking for at 50 is different than 25. It's no longer love at first sight when you meet someone at 50 I find. It has gone against me, seeing all of these stunning escorts who are sexually uninhibited for the last 25 years, as it has influenced how I look at civilian women. It has definitely made me a lot more picky, which resulted in me being single for pretty much my entire life.

I've met a lady who is the same ethnic background as me, who has been in Canada for 5 years and is in the final stages of getting her permanent residency card. She married after only 6 months of meeting her husband, as she was quite religious at the time and societal pressures really pushed the tradition of marriage. She is still religious, but now only hopes to meet a man who has good morals, as her former husband was supposed to have been a good Christian, but cheated on her at least once. She was a professional musician, and I guess she had a mid life crisis, in part because of her husband's infidelity and moved to Canada with her two children to start over. They are now in grade 9 and first year university respectively, and are open to their mother dating again.

One of the biggest concerns I have is her financial situation. Unfortunately, as a first generation immigrant, her employment opportunities aren't that good. She's working as a cook right now, but hopes that once she gets permanent residency, she can start teaching music full time. Because of child support, she was able to purchase a townhouse, and drives a small new Toyota SUV. She does not appear to be in urgent need of money, as she only works 24 hours a week. All of her children's education costs seem to be taken care of.

Her father was a university professor who died early, and her mother was a school teacher. She was well raised, and is an agreeable person to be around. In part because of her previous profession as a concert musician, she had to be reasonably attractive and lead a healthy lifestyle to make the audition cuts. She also does not appear to have a wandering eye as she went 5 years without seeing anyone and concentrated on raising her children.

My concern is her lack of any real career prospects and some communication issues. I don't want to hold that against her as her English is better than my understanding of her native language, and because my parents were first generation immigrants, and also had limited opportunities, but it is in the back of my mind.

I have a lot to lose, as I earn over $100,000 a year, am mortgage free, and have been contributing to my retirement since I was 20 years old. I'll also have a 50% pension in ten years. A lot of things seem like they line up, but am wondering if I am making the financial issue a bigger deal than it should be? When I look at her, I'm constantly wondering if this would work out.
 

Leimonis

Well-known member
Feb 28, 2020
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so what exactly are you looking for, except to lose your house and make a couple of lawyers happy?
 

poorboy

Well-known member
Aug 18, 2001
1,268
105
63
so what exactly are you looking for, except to lose your house and make a couple of lawyers happy?
That is a good question.

I don't think it's a good idea to be a 50 year old bachelor. I've actually had a long term regular fill in for a "girlfriend" for work issues in an effort to look "normal". I've pretended to be in a relationship so I don't get shafted on a transfer. Women are also less likely to be looking at filing a complaint against you as they don't feel like you are creeping on them if they think you are in a relationship and are more relaxed around you because they feel you are not going to hit on them. Not only does being single affect your career, it would be nice to have a travelling companion and someone to spend retirement with.
 

jcpro

Well-known member
Jan 31, 2014
24,670
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Tell her about your hobbying and see where she stands on that morality thing. If she compromises, run.
 

chodge

Well-known member
Feb 20, 2004
2,246
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I've been on three dates with the same woman now. What you're looking for at 50 is different than 25. It's no longer love at first sight when you meet someone at 50 I find. It has gone against me, seeing all of these stunning escorts who are sexually uninhibited for the last 25 years, as it has influenced how I look at civilian women. It has definitely made me a lot more picky, which resulted in me being single for pretty much my entire life.

I've met a lady who is the same ethnic background as me, who has been in Canada for 5 years and is in the final stages of getting her permanent residency card. She married after only 6 months of meeting her husband, as she was quite religious at the time and societal pressures really pushed the tradition of marriage. She is still religious, but now only hopes to meet a man who has good morals, as her former husband was supposed to have been a good Christian, but cheated on her at least once. She was a professional musician, and I guess she had a mid life crisis, in part because of her husband's infidelity and moved to Canada with her two children to start over. They are now in grade 9 and first year university respectively, and are open to their mother dating again.

One of the biggest concerns I have is her financial situation. Unfortunately, as a first generation immigrant, her employment opportunities aren't that good. She's working as a cook right now, but hopes that once she gets permanent residency, she can start teaching music full time. Because of child support, she was able to purchase a townhouse, and drives a small new Toyota SUV. She does not appear to be in urgent need of money, as she only works 24 hours a week. All of her children's education costs seem to be taken care of.

Her father was a university professor who died early, and her mother was a school teacher. She was well raised, and is an agreeable person to be around. In part because of her previous profession as a concert musician, she had to be reasonably attractive and lead a healthy lifestyle to make the audition cuts. She also does not appear to have a wandering eye as she went 5 years without seeing anyone and concentrated on raising her children.

My concern is her lack of any real career prospects and some communication issues. I don't want to hold that against her as her English is better than my understanding of her native language, and because my parents were first generation immigrants, and also had limited opportunities, but it is in the back of my mind.

I have a lot to lose, as I earn over $100,000 a year, am mortgage free, and have been contributing to my retirement since I was 20 years old. I'll also have a 50% pension in ten years. A lot of things seem like they line up, but am wondering if I am making the financial issue a bigger deal than it should be? When I look at her, I'm constantly wondering if this would work out.
Ladies I have met in the older age group 45 to 60 I find are over weight and not into any type of fitness , have minimal savings and are renting and have no car

If they have any of these these they were probably married a some point and got half when they got divorced so they end up owning a home and the job they do have pays mostly for the existing house while they collect from their ex So I would stay single
 

Leimonis

Well-known member
Feb 28, 2020
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That is a good question.

I don't think it's a good idea to be a 50 year old bachelor. I've actually had a long term regular fill in for a "girlfriend" for work issues in an effort to look "normal". I've pretended to be in a relationship so I don't get shafted on a transfer. Women are also less likely to be looking at filing a complaint against you as they don't feel like you are creeping on them if they think you are in a relationship and are more relaxed around you because they feel you are not going to hit on them. Not only does being single affect your career, it would be nice to have a travelling companion and someone to spend retirement with.
I don't even know where to start. A lot of men gave up half of what they had to be in a position you are in right now.

You can travel the world with sugar babies or you can travel the world with an old woman who prohibits you to sleep with younger women. Literally for the exact same price, i.e. you pay for tickets and hotel and incidentals.

As far as career goes, so you gonna be making maybe an extra what $20K on top of your current $100K, which is like extra 10K after taxes? Is that going to make a difference in your lifestyle? And you have to pretend to be happy for that money? You think your wife will not suck this and a whole lot more out of you in one form or another?

I am shaking my head...
 

angrymime666

Well-known member
May 8, 2008
1,104
666
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its a slipper slope man.

there are so many red flags especially the financial one, and you are not even married. you could be on the hook for alimony and child support if you enter into a relationship with her even if you do not tie the knot.

as a guy approaching 50 Ive had long tern girlfriends, fuck friend, etc. usually at the 2 year mark I lose interest in them since you know the good and the bad about them. the more I get to know a person the more I dislike them. I dont date anymore, its just a really poor return on investment in terms of finances and risk.

if I want sex I go in leo, or go pooning in another country and have short term girlfriends. I get the gfe and can avoid the risk.

from what Ive read from your post I dont get the vibe that you are that into her since you are posting your concerns here and it doesnt seem you have that infatuation for her that lure us men in for a long term relationship. if you are already questioning I think thats a good indicator that shes not for you.
 

danmand

Well-known member
Nov 28, 2003
46,821
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If your concern is about your money, I dobut it is the right thing for you. (Says somebody who has two divorces behind him)
 

WetSeeker

Well-known member
Jun 23, 2020
592
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You have had 3 dates and are thinking long-term already?
Most men that went through a bitter and costly divorce would want you to give your head a shake.
You are not there to rescue anyone from their own screw-ups (I have been guilty of that and it always ended badly)
Go on dates but go slow, make yourself a promise to not move-in together and stick to it. Give it at least a year.
Anything you gain from the time you cohabit is at risk. Not your accumulated wealth but certainly 50% of the next 10 years pension and savings could be at risk.
Your home is also at risk if she can claim a dependence. Best to maintain separate households.
Do not move in unless you have a cohab agreement and see a lawyer first to understand what is at risk.
Good luck
 

Twister

Well-known member
Aug 24, 2002
4,696
441
83
GTA
At that age it becomes more lf you're compatible to live together and have the same interests.
 

JethroBodine

Well-known member
Feb 4, 2021
2,482
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Tell her about your hobbying and see where she stands on that morality thing. If she compromises, run.
Don't listen to this stupid shit. Fucking imbecile.

Seems to me, after hobbying for 25 years you're getting a little bored or lonely, having had your fill of hot, young pussy, and want to see how the other half lives. Sure, older women can't compete with SPs in terms of sex appeal, but they have more to offer in regards to companionship, common interests and a spiritual connection, which it seems you are seeking.

Three dates is way too soon to be thinking marriage. Give it at least a year, if not longer. Sure, you're 50, but you've waited this long, so what's the rush?

I wouldn't move in with her. I'd do some overnighters, either your place or hers (if the kids are away) to get a feel of what it might be like.

I understand your fear of taking a big financial hit if things go south. But there comes a time when you start to worry about spending your golden years alone and realize "Yeah, I've spent my life accumulating all this money and I'm well off, but now I'd like to share it with someone special."
 

Robert Mugabe

Well-known member
Nov 5, 2017
9,788
6,828
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That is a good question.

I don't think it's a good idea to be a 50 year old bachelor. I've actually had a long term regular fill in for a "girlfriend" for work issues in an effort to look "normal". I've pretended to be in a relationship so I don't get shafted on a transfer. Women are also less likely to be looking at filing a complaint against you as they don't feel like you are creeping on them if they think you are in a relationship and are more relaxed around you because they feel you are not going to hit on them. Not only does being single affect your career, it would be nice to have a travelling companion and someone to spend retirement with.
Sounds like you've thought through all the answers to questions that never came up. Maybe your handle portends your future with this girl. At that age wouldn't you get bored with her after about 3 dates with fucking involved? after 25 years of "stunning" working girls.....who know how to work ?
Since you asked. Marry her. what could go wrong?
 

xix

Time Zone Traveller
Jul 27, 2002
4,335
1,487
113
La la land
Wow she is not for you, since you are not ready as mention above.
- She does get some money from her ex' University. There was an article a few years ago where a guy was getting it as his wife passed away but they found he killed her.
- Musician / Artist never make money unless she is a Hollywood star and that is bleak.
- If you move together you loose half your money instantly.
- If she finds out about your pooning life, you are done, Remember she is Religious.
- I blame this depression on COVID-19. I was thinking last week about getting involved, But I come back here to be reminded why I chose this lifestyle. People can only act for so long.
- HOW can someone working 24 hours min wage per week and have a house and still pay for the upkeep of the place? - see line 1
- I agree with danmand - MONEY on you,
 

JethroBodine

Well-known member
Feb 4, 2021
2,482
7,188
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This is a great site to get escort and massage reviews. This is a really dumb place to get life advice.
Right. I mean, guys who pay for pussy, what could they possibly know about life experiences after lessons learned from their ups and downs through relationships, good and bad, and (likely) marriages, as opposed to the balanced views he'd get from the guy who's been in a stable marriage for 20 years and hasn't dated in two decades.
 

xmontrealer

Well-known member
May 23, 2005
10,275
7,729
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50 and never married. Probably marriage is not for you. Your excuse is that hot working ladies spoiled you for civvies?
How in the world do you think you'll be happy with one dish on the menu for the rest of your life?

She is looking for a man with "good morals" and was hurt by her ex who cheated on her once...
Do you plan to be 100% faithful, or will you be just like her ex but worse?

You're already worried about what will happen financially both in a marriage with her and in case of divorce.

At no point in your original post do you say why you are even attracted to her and considering marriage, apart from having the same ethnic background.

I really don't see any chance for a successful long term relationship here, let alone marriage.
 

wazup

Well-known member
Jun 12, 2010
4,280
582
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Do you want to be with someone who actually wants to be with you (her), or with girls who pretend to like you as their job (sp)? Providers are great don't get me wrong but they pretend to enjoy our company, it's their job.
 
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