My Best Friend and My Son Want to Date. Help! What should I do?

[Anonymous]

Just a few days ago, my son (25) and my best friend (39) told me they have strong feelings for each other and want to date. (I'm 45, by the way) They initially resisted out of concern for how it might affect me, but ultimately, their feelings became too strong to ignore. They assured me they care about me and want to maintain our relationship.

I'm still in shock and trying to process this. On one hand, I want to be supportive, but I have so many concerns, especially about the age gap. She has an established career while he’s in graduate school, so they’re at very different life stages. I worry their priorities might clash—he’s exploring his path, while she might be looking for a stable partner. What if she pressures him about having kids? I know she wants them, but I fear he might not be ready, and that could create issues down the line.

I’m also anxious about how their relationship could affect my bond with both of them. If things go south, I know they wouldn’t want me to take sides, but emotions can run high. What if he feels hurt and pulls away from me, or I lose my friend? The thought of navigating these raw feelings is overwhelming.

If they make this work, the dynamic will be awkward. How do I balance support with my own discomfort? I can already imagine the tension at family gatherings. Plus, there’s the judgment from friends and family regarding their age difference. It feels like our relationships could become the subject of gossip, which adds another layer of stress.

On a personal level, this just feels wrong. My best friend dating my son? It crosses a boundary that leaves me uneasy. I wish things were simpler. If they didn’t work out, I could preserve my relationships without added complexity. If they do, it might amplify the weirdness (last part of the question continued if you click)

Updates

1 y

I want them to be happy, but I’m overwhelmed by how this might change everything for us. I need to find a way to navigate this without losing the closeness I cherish. How should I process this? Is their relationship a good idea, or a mistake? How can I maintain strong connections with both of them in this strange situation? What’s the best approach for me moving forward?

Updates

1 y

Also, to clarify, they did not meet when my son was a kid. They met when she was 36 and he was 22.

[Finchie40]

Unfortunately you are shit out of luck on this one , you can either accept it or not accept it at this point , but no matter what you decide? it isn’t going to stop them from wanting each other , my advice to you is just accept it for what it is , because they are both adults , Age doesn’t really mean shit when it comes to loving someone , so just ignore the people that say it does , they don’t know shit. They are just trying to rub their 2 cents together thinking they know the answers , but they don’t , so just ignore the negative remarks and stay out of their relationship i as much as possible , I know it’s fucked up , but stay out of it as much as you possibly can. and just sit back and watch what happens , just let them know you don’t want to be dragged into any of this if things go bad between them , tell them you love them both but you will not be in the middle if things get out of hand. Just support them and be happy for them as much as possible , if thongs don’t work out between them? all you have to say is I told you so but you didn’t want to listen. And when push comes to shove blood is thicker than water , so be there for your son as much as possible. but as for your friend? kick her to the curb if she hurts your son’s feelings.

[Asker]

But what if things do work out? I actually might be more worried if that's the case

[Finchie40]

Just be happy for them , what mother in law likes her daughter in law lol

[Finchie40]

Between you and I , it’s probably not going to last , if it does? Then be happy for them but be prepared for it more than likely not going to last , so just let them have their fun and sit back and watch , we can’t predict the future but the chances of them making it the long haul are very slim. One of them will either cheat or meet someone else because of that age gap , but I could be wrong , so just sit back and watch and be happy for them

[Finchie40]

Anything you say to them is going to go in one ear out the other anyways , so don’t waste your time and energy trying to convince them on whether they are right or wrong , whatever happens in their relationship is between them. Just let them both know you aren’t going to be stuck in the middle of things don’t work out between them and keep it at that. I had a friend that was 30 at the time and he met a girl that is old enough to be his mom like 53 years old 20 years later , they are still happily married , she is 73 and he is 50 , they are both still happy with each other

[Anonymous]

I don’t think it’s a good decision. But no matter how much you tell someone they have to learn from experience. I’m not going to lie as a man if I was getting into w an older women her age I’d be all for it, but nothing serious. Actually I was in a situation like that. I was in my early 29s, she was about your age. It was purely sexual, nothing more. I think the one who you should try to appeal more to would be your best friend. She’s older. She’s been an adult much longer than your son has. Not that just because someone is older they know better. I’d hope she would. But maybe not. I’d try talking to her more than your son. Your son is going to do what he wants to do most likely, especially as a man. I think you have a better chance of expressing to your friend how it makes you feel. Woman to woman. She should be able to understand you more as a woman herself I would hope. Does she have children? Has she ever been married? This is a hard call. You can’t really forbid them to do it, they’re both adults. But what if she cheats on him? You’re not going to be happy w her? I don’t think there’s much you can do but maybe talk to your friend. They’re going to do it regardless of what you say if that’s what they decide.

[Asker]

She was married a while ago, but she's been divorced. She doesn't have kids (but she really wants them, which is why I'm concerned she might pressure my son into having kids before he's ready)

I don't know if that changes anything though

[Opinion Owner]

Ok. Why is she divorced now? Is she cute? I don’t mean from a female’s perspective. Women don’t like hurting each others feelings most of the time so they always say all women are beautiful. I’m talking from a man’s perspective? Did she have a lot of men after her?

[MK1997]

Don't listen to those saying do nothing. This is a horrible decision your son is making.

You must stop them. Don't be direct but warn your son of dangers like growing old with a woman 14 years older, how it will impact him. Warn him of now it will impact his kids and show him the benefit of younger girls. Introduce girls to him or try to have girls to seduce him.

I agree it's innapropriate from her. And if she was my friend I wouldn't be her friend anymore, or at least slowly distance myself. Don't show her support or anything like that. She doesn't deserve it.

[Asker]

Part of the reason why I'm really unsure/confused right now is that I have feelings in both directions. Are there potential downsides of being with someone a lot older? Yes. However, every relationship has its risks. Also, I don't doubt that there are relationships with big age gaps that work out for people. Moreover, if we reversed the genders would this be viewed as being as much of a problem? My guess is 'no'.

Yes, the relationship is super weird and makes me super uncomfortable. But does that mean my friend (or my son) has betrayed me? She hasn't hurt him (at least as of now). He seems to want to be with her just as much. Moreover, other than making me super uncomfortable/confused/weirded out by having a relationship with each other, neither of them have hurt me. In fact, they came to me to let me know because they were concerned about how I'd feel.

I'm still trying to process this, but I know I don't want to cut either of them off for this. Maybe I'll advise against it, but I certainly don't want to say 'you break up, or our relationship is over!'

[MK1997]

Encourage him to find someone younger. I couldn't be friends with her, to me my son would be a person my friends can't get involved with.

[HelpfulWoman]

has your friend been around your son while they were a kid/minor? if so, its weiiiiiiiiiiiiiiiiiird

[Asker]

No. She met him when she was 36 and he was 22.

[HelpfulWoman]

then not really an issue.
is your friend not a good person? is your son not a good person?
if no to both, then feels weird to say they're not "allowed" to date.

[SuchSightsToShowYou]

Your son wants to bang your best friend, and your best friend is apparently fine with it.

Did you ask either of them how long this has been going on, or how it started, or anything like that? You might get more honest answers if you asked one of them when the other wasn't nearby. Would it bother you more if there had been an attraction between them for years?

Are you worried that your best friend is taking advantage of your son?

They don't seem to be asking your permission to date, so there's not much you can do, even if you disapprove. So at least you don't have to worry about what you SHOULD do.

Does your best friend have a son? Could you maybe date him, to even things out?

[Asker]

They've been attracted to each other for about as long as they've known each other. I knew about it, but I thought it was just a 'they think the other person is attractive, but they know nothing is going to happen', so it never bothered me. I never thought something actually would happen.

However, they've only been 'going out' for about a month.

I think she likes going out with a much younger guy. I think it makes her feel more attractive. But I don't think that's necessarily her taking 'advantage' of him.

[SuchSightsToShowYou]

So she's not taking advantage of him. Do you think he might be taking advantage of her? Or not taking advantage of her, but do you think he might see her as sort of a "hot milf" fantasy? Something like that?

Has your friend said anything about seeing your son as a potential father for her potential children? Or like implied anything?

Would it upset you if they became a long-term couple? Would it gross you out?

[Nirmroth]

Nothing really. If you go against them they will likely only want to be toghether even more but now you're the bad one.

Best position you could be in would be a neutral one in this situation. Dont talk behind their back but you dont need to defend them either its their choice, theyre old enough to know the consequences (at least one of them)

[DrPepper12]

I only have three iron clan "no go" for a relationship:
Is it legal?
Is it consensual?
Is intimacy conducted safely?

After that, it's none of my business. I know that's harsh and not what you want to hear but it's just one person's opinion. No matter what happens with this relationship, I think you should see a therapist to help work through these feelings and anxieties.

[BetaBucks]

They won't last long. She's just a horny older lady and you son probably struggles a bit with the ladies. It works out well for both of them. The fuzz will wear off pretty quick though. You probably just have to let it play its course.

[RingOfFire]

It's never going to work out. But there isn't much you can do about it because they're both adults and they make their own decisions.

I would just encourage him not to rush into making a long-term commitment and give it time.

[Mati91]

Give them your blessing cause they might go behind your back. But also tell them you’re not gonna take sides if it goes south. And if your son not ready for children. Tell her that.

[Asker]

Well, the children thing is a bit more complicated. I'm pretty sure she's not going to try right away. So if I tell her 'he's not ready for kids yet' she'll just say, 'Oh, I know. We're not going for anything right now'.

However, she really wants kids very badly, and she knows her clock is ticking. He wants kids too, but I think that he thinks it might be a more 'down the road' thing for him. However, I'm worried that she'll eventually push him into that before he is ready (which isn't now, but it could be a few months from now)

[noohair]

In the end it is none of your business. These are two adults. If you insert yourself in this and try to influence either of them, you will wind up losing. Good Luck.

[Juxtapose]

They are both legally adults so this is out of your hands. Let it happen and if it bothers you enough go see a therapist.

[LiamJHayden]

Let it be. If things go south, you side with your child.

[kareka]

Tbh let them...
I think they are old enough..
I mean date with you are on track better than behinde you...

[zombiewoof]

Let them figure it out, just hope if it ends there are no bad feelings

[20yearsolder]

They're both adults, let it happen

[Pterodon]

Let them