Anonymous
Post 12/19/2025 16:54     Subject: 19 year gap - Will everything be okay?

On the plus side if the prenup is generous she can get out with some money and find a younger guy later.
Anonymous
Post 12/19/2025 16:53     Subject: Re:19 year gap - Will everything be okay?

It sounds like he s..cks as dad to his existing kids. It won’t be any different to your children, OP. And do have a lawyer if you sign a prenup - he should be talking about your trust not a prenup at this wealth level
Anonymous
Post 12/19/2025 16:49     Subject: 19 year gap - Will everything be okay?

No one knows what will happen.

I have two friends who marrried men who were 15-20 years older than them.

the first one -- he already had three kids, he said he wanted to have kids with her, but he wasn't at all enthusiastic about it so they never ended up doing it. SHe also had a lot of drama with the step kids and a LOT with the ex wife (with kids, this person never goes away). They divorced when she was near 40 and she never ended up remarrying or having kids.

They actually love each other and stay in touch. But the marriage was so complicated. I wonder if she would do differently if she could go back in time.

the second person married an extremely high net worth person, like $16 million penthouse in NYC. she had two kids with him and then really disengaged from him and became less interested in him. They grew apart, divorced in her early 40s, now she has 50 percent custody and a new partner.

She does love her kids and Im sure she wishes she had them 100 percent of the time. I also dont know if she has regrets. But definitely a more complicated path than marrying someone who will be a partner for life.
Anonymous
Post 12/19/2025 16:47     Subject: 19 year gap - Will everything be okay?

His health and body will start more rapidly deteriorating soon. I’d bank on another 10 years of things going fairly smoothly but if this is something you are actually going to go along with be aware that there are likely going to be physical limitations and health issues that will come up often and for decades.

Personally, I’d be more worried about the blended family complexity
Anonymous
Post 12/19/2025 16:43     Subject: Re:19 year gap - Will everything be okay?

Anonymous wrote:OP: I don’t believe that finances will be an issue. He has a $26m NW (BigLaw & generational wealth) and he’s promised me a prenup. His kids (17/g & 14/b) like me (though some might think I’m closer in maturity to them, I’m more aligned with him in terms of maturity and life perspective). I don’t have daddy issues—My dad is a great dad, not all women who date older do, I just prefer older. I’ve dated older men since college (not seriously) but I never expected to fall for one. Now I love him, we’re making plans and he wants more, marriage soon and kids as early as possible.
Health during old age is my biggest concern, not old age itself. While he’s healthy now and doesn’t have major health issues in his family (parents are early 70s and pretty healthy), I can’t ignore the fact that the age gap means he’ll be much older health wise and I’m unsure if that’s what I want long term. I’m hoping for at least 20 more years of good health though, but that isn’t guaranteed.


Your biggest concern should be why this guy wants a do over family. That’s not a normal thing to do. It happens, with grandparents raising kids and such. But if a man is setting out to do that, that is such a red flag.
Anonymous
Post 12/19/2025 16:40     Subject: 19 year gap - Will everything be okay?

Yeah, no way. I definitely would not do this.

It seems like you haven't really thought through the parenting. You are signing up to be a stepmother. You will be stepmother to his children. That means that if anything bad happens to their other parent, or if they just decide they want to, they'll be living with you full-time. Teenagers can be really, really difficult. And they can be really, really expensive. People say "Little kids, little problems-- big kids, big problems" and it's absolutely true. Mental health, eating disorders, drugs, trouble with the law, trouble with boyfriends/girlfriends, any number of things can seriously derail a teenager and cause a huge stress on the whole family. And you'll be dealing with his ex quite a bit more than you thought.

Your kids will be #3 and #4. You won't have the first-time parents experience-- and he'll think he knows better than you about all kinds of parenting things, even if his opinions are out of date. Third and fourth children in a family don't get as much attention. They spend their weekends at high school soccer tournaments. They tag along on college visits. If this makes you say "Yay, I would love for my kids to be #s 3 and 4 in a big family", then great. But go in with eyes wide open.

The older kids will go to college, and they'll probably be pretty low-maintenance for a while. But then there will be graduations, moves, engagements, first house, wedding, first grandchild, second grandchild-- and they'll be wanting their father's time and attention (and maybe money). They might want to move back in with their dad, it's more common now than you think. They'll want him to play the doting grandpa and come to their games and piano recitals and everything, even as you're expecting him to be a very engaged father to your kids as they become busy tweens and teens. And that's the best-case scenario! If anything actually bad happens-- any medical crisis, any serious trouble with the grandkids, whatever, they'll want their father's support. Really, really think whether this is something you envision for yourself.

And after all of that, he'll be old and you'll care for him, and then he'll be too old to care for you.
Anonymous
Post 12/19/2025 16:35     Subject: 19 year gap - Will everything be okay?

I know 2 women who married guys who are much older and on their second families. They are super sensitive about it and talk about it all of the time. And the kids are super sensitive about their dad being grandpa age and often confused for a grandpa.
Anonymous
Post 12/19/2025 16:27     Subject: Re:19 year gap - Will everything be okay?

My sister did this. She had to nurse him through Parkinson's, which killed him. I'd take a hard pass. Are you expecting to be geographically mobile in order to put your degree to use? You probably will put your education on the backburner if his money is always around as a cushion.
Anonymous
Post 12/19/2025 16:26     Subject: 19 year gap - Will everything be okay?

Anonymous wrote:No way would I take this deal. I’m so sorry because I realize you are seriously considering this and must be emotionally invested but this sounds terrible.

If this is a gold digger thing and he is filthy rich and that’s the play, it’s not my thing, but I get that. If he’s a regular old divorced guy with teens I sincerely hope you can do much better and that you do.

I don't know if it's worth the money. It sounds like op is into old guys. She may have never experienced the strength, passion and physical beauty of a fit man her age. Op, you are missing out. Get with a young man and eventually, he'll have that elderly dad bod you crave.
Anonymous
Post 12/19/2025 16:25     Subject: Re:19 year gap - Will everything be okay?

Anonymous wrote:OP: I don’t believe that finances will be an issue. He has a $26m NW (BigLaw & generational wealth) and he’s promised me a prenup. His kids (17/g & 14/b) like me (though some might think I’m closer in maturity to them, I’m more aligned with him in terms of maturity and life perspective). I don’t have daddy issues—My dad is a great dad, not all women who date older do, I just prefer older. I’ve dated older men since college (not seriously) but I never expected to fall for one. Now I love him, we’re making plans and he wants more, marriage soon and kids as early as possible.
Health during old age is my biggest concern, not old age itself. While he’s healthy now and doesn’t have major health issues in his family (parents are early 70s and pretty healthy), I can’t ignore the fact that the age gap means he’ll be much older health wise and I’m unsure if that’s what I want long term. I’m hoping for at least 20 more years of good health though, but that isn’t guaranteed.


$26m isn't that much when you subtract three (four?) college tuitions, the cost of raising one or two more kids, plus his retirement and eldercare, plus yours. This is where people get into a crunch-- he's getting a lot closer to the end of his working years (because you can't assume he'll be healthy enough to work until 67 or whatever), and his expenses are about to spike.

I think the main problem people run into is that there's not enough dad to go around. How is he going to parent young kids with the level of hands-on a woman your age expects, plus also be a good father to his teenagers, plus also work enough to pay for all of this? It's a lot and he's only going to be less and less energetic. People get into these situations with the best of intentions, but sometimes the circle just doesn't square. Having a lot of money helps, but it's also just one more thing to fight over-- and believe me, his teens will eventually figure out that their inheritance decreased dramatically when you married and with each subsequent child. People will flame me for this and say nobody's entitled to an inheritance, which is true, but you can't show up in their lives and do that and expect them to be happy about it. You need to be realistic.

Assuming your PhD isn't going to get you a high-income job...
Anonymous
Post 12/19/2025 16:25     Subject: Re:19 year gap - Will everything be okay?

Anonymous wrote:He been divorced for eight years (been together 1.5), he has two kids who are 17 & 14, and he does want kids with me.


Ohhhh, this is the grossest type of men to me. Second family dudes.
Anonymous
Post 12/19/2025 16:24     Subject: Re:19 year gap - Will everything be okay?

Anonymous wrote:OP: I don’t believe that finances will be an issue. He has a $26m NW (BigLaw & generational wealth) and he’s promised me a prenup. His kids (17/g & 14/b) like me (though some might think I’m closer in maturity to them, I’m more aligned with him in terms of maturity and life perspective). I don’t have daddy issues—My dad is a great dad, not all women who date older do, I just prefer older. I’ve dated older men since college (not seriously) but I never expected to fall for one. Now I love him, we’re making plans and he wants more, marriage soon and kids as early as possible.
Health during old age is my biggest concern, not old age itself. While he’s healthy now and doesn’t have major health issues in his family (parents are early 70s and pretty healthy), I can’t ignore the fact that the age gap means he’ll be much older health wise and I’m unsure if that’s what I want long term. I’m hoping for at least 20 more years of good health though, but that isn’t guaranteed.

My brother is 17 years older than his wife. She's now 38 and fighting aggressive stage 3 breast cancer. You never know what future health will be, but there's no way my brother could care for her and their kids if this happened in 5+ years. He's managing work, her health needs, kids, the house, etc. Just another angle for you to consider.
Anonymous
Post 12/19/2025 16:17     Subject: 19 year gap - Will everything be okay?

Anonymous wrote:
Anonymous wrote:
Anonymous wrote:I’m 27 and a PhD student, and my boyfriend is a 46 year old lawyer. I really love him, we have an amazing relationship - we communicate well, have similar goals, compliment one another and enjoy being together. That said, sometimes I worry about our age difference and what it might mean for us long term.

I’d love to hear the perspectives of people who’ve been in or are in relationship like this


Say you get married and he knocks you up a couple of times and you push out your sprogs when you are like 32 and 35. He'll be like 61 and 64. Which means the odds of him becoming worm food before your child reaches the age you are now are very high.


And before he becomes worm food, he'll become a grouchy old man (and his bad mood will be aggravated by teenagers in the house, as they are almost always aggravating) with health problems, and OP will be a caretaker for teenagers and a grouchy old man at the same time.

and be going through menopause and caring for aging parents.
Anonymous
Post 12/19/2025 16:13     Subject: 19 year gap - Will everything be okay?

No way would I take this deal. I’m so sorry because I realize you are seriously considering this and must be emotionally invested but this sounds terrible.

If this is a gold digger thing and he is filthy rich and that’s the play, it’s not my thing, but I get that. If he’s a regular old divorced guy with teens I sincerely hope you can do much better and that you do.
Anonymous
Post 12/19/2025 16:08     Subject: Re:19 year gap - Will everything be okay?

OP: I don’t believe that finances will be an issue. He has a $26m NW (BigLaw & generational wealth) and he’s promised me a prenup. His kids (17/g & 14/b) like me (though some might think I’m closer in maturity to them, I’m more aligned with him in terms of maturity and life perspective). I don’t have daddy issues—My dad is a great dad, not all women who date older do, I just prefer older. I’ve dated older men since college (not seriously) but I never expected to fall for one. Now I love him, we’re making plans and he wants more, marriage soon and kids as early as possible.
Health during old age is my biggest concern, not old age itself. While he’s healthy now and doesn’t have major health issues in his family (parents are early 70s and pretty healthy), I can’t ignore the fact that the age gap means he’ll be much older health wise and I’m unsure if that’s what I want long term. I’m hoping for at least 20 more years of good health though, but that isn’t guaranteed.