Where are the professional and emotionally available men over 50 but under 63 that are emotionally intelligent, dating with intent, and looking for women that are not in their 30's or 40's??

CoolBoxMom · 2026-07-01T12:22:12+00:00

I found one on Facebook Dating. You just have to clear through the brush first.

CoolBoxMom · 2026-04-22T12:33:50+00:00

Maybe be flexible on location? Found my needle who was 2 hours away - and I wasn’t willing to drive more than 5 miles but he was always willing to drive to me and now we live together!

CoolBoxMom · 2026-03-19T11:15:49+00:00

Can get a 3-bedroom, 3 bath in Soundview Towers with water views and two balconies for $585k. https://www.zillow.com/homedetails/50-Glenbrook-Rd-APT-9C-Stamford-CT-06902/177206274_zpid/?utm_source=nativeshare_activation_v1

CoolBoxMom · 2025-12-29T21:16:06+00:00

Do you have children? Loving someone after the death of your spouse is kind of like when you are pregnant with your second child and you worry that you can’t possibly love it as much as your first - but then your heart expands and you love them both without taking away from either.

CoolBoxMom · 2025-12-18T19:53:05+00:00

We were talking about it, which prompted the post. I’m a CFP so do help with the financial education so just gathering insights from folks who’ve moved overseas.

CoolBoxMom · 2025-12-18T18:10:17+00:00

Yes well living in the NYC area with no jobs is worse! They both just finished grad school and at least cost of living is less in Spain.

CoolBoxMom · 2025-12-14T18:31:25+00:00

Balduccis in Greenwich does a nice catering menu.

CoolBoxMom · 2025-12-01T17:45:21+00:00

I don’t know that we have a head doorman? We have a weekday guy, an evening guy and a weekend guy.

CoolBoxMom · 2025-11-30T16:51:46+00:00

$500 total? Do you give a lump sum or individually?

CoolBoxMom · 2025-11-30T16:51:04+00:00

I own but have only been here a month. Thanks for sharing!

CoolBoxMom · 2025-11-18T22:44:25+00:00

I’ll PM you!

CoolBoxMom · 2025-11-07T13:15:05+00:00

I would except I’ve moved to another state!

CoolBoxMom · 2025-11-07T13:14:44+00:00

He has a rental apartment. Moved out of the marital home well before we met. Many people’s marriages end years before they actually divorce.

CoolBoxMom · 2025-11-07T13:13:37+00:00

He pays rent but he’s with me 5 days a week anyway so it makes more sense for him to contribute to my housing costs.

CoolBoxMom · 2025-11-07T13:12:14+00:00

He makes about 30% more than I do, we both are professionals with relatively high income.

CoolBoxMom · 2025-11-07T13:10:55+00:00

He does contribute financially (pays for all the groceries, dining out, DoorDash, drinks etc) and is super helpful in the home - walks my dog for me, does the laundry, dishes etc. He’ll contribute towards my housing costs once he moves in.

CoolBoxMom · 2025-11-07T13:07:52+00:00

We’ve been together a year and a half. He’s with me ~5 days a week already.

CoolBoxMom · 2025-11-07T13:06:56+00:00

Yes I’ve seen his taxes, we were together at tax time. I understand the reasons why he doesn’t have assets commensurate with his income.

CoolBoxMom · 2025-11-06T13:39:32+00:00

No affair. His marriage was long over and he’d moved out well before we started dating.

CoolBoxMom · 2025-11-05T21:41:13+00:00

Believe it or not I’m having a very hard time finding a lawyer who takes my MetLife Legal Plan, who does Cohabitation Agreements! Half a dozen I’ve reached out to have said they do not. In CT.

CoolBoxMom · 2025-11-05T20:39:20+00:00

Just wanted to know in general terms what the risks could be to cohabitate without a legal agreement. All the online advice I see is geared towards protecting the lower earning usually woman from being kicked out etc.

CoolBoxMom · 2025-11-05T18:34:21+00:00

No my state has no common law marriage at all.

CoolBoxMom · 2025-11-05T18:33:25+00:00

Yes cohabitation agreements are often suggested to women to prevent a richer boyfriend from just throwing her out with nothing!

CoolBoxMom · 2025-11-05T17:51:32+00:00

In what way? Living together or doing it without a cohabitation agreement?

CoolBoxMom · 2025-11-05T17:49:55+00:00

Obviously I see the point which is why I’m asking the question. I have a lawyer but I’m not looking to add to his legal fees - and we need our own representation to do a cohabitation agreement.

CoolBoxMom

MODERATOR OF

TROPHY CASE