Wanting to Date and Have Sex With a Friend's Sister

[davidsonj73]

I am 62, he is 45, and she is 37. I met her once, we had chemistry, the problem is I don't want to mess up the friendship I have with my friend. Any advice? She is a single mother. I don't mind single mothers, I just mentioned it because it might be relevant. Perhaps I can offer to teach her son some martial arts? We are all three are into balancing our chakras. I wouldn't mind having a long-term/exclusive relationship with her. I actually had a conversation with this friend about the kind of women we are into, I told him that I am interested in dating women ages 25 to 45 (really its 18 to 45), and he said that he would date women ages 25 to 50. We both said that we would be interested in single mothers. He winked at me, I think he knows I like his sister, but then again, he is also bisexual. He lives with his sister. She is beautiful! Anyway, I only met her once but I'm thinking of being bold and telling him: "I thought your sister was cute when I met her!" He could steer the conversation a different way and I would never bring it up again, or he might say: "You know, she's single." And then I ask him to give her my phone number, and then it's in her hands. Another male friend told us both that he would never date or be interested in a single mother.

 

[davidsonj73]

What would you do if you were in my situation? Please see above. I am the OP.

 

[CAPSLOCK BANDIT]

Being timid at 18 is understandable.
Being timid at 62 is a condemnation.

Are you sure he wasn't smiling cause he thinks your into him or something, like homie knows you like women, right?

Like, what has compelled you to offer her son marital arts training instead of herself? This is the perfect activity to show off your skill and escalate, yet your choosing to steer away?

This post is so outlandish it's almost too obvious of a troll to be a genuine troll

 

[BaronOfHair]

I am 62, he is 45, and she is 37. I met her once, we had chemistry, the problem is I don't want to mess up the friendship I have with my friend. Any advice? She is a single mother

The "Stop, Do Not Enter" sign just appeared. Now it's incumbent on you to heed it

 

[SW15]

It's a normal feeling to want to have sex with a male friend's sister. I have had that feeling on at least 2 occasions since I became a legal adult. I never acted on it. Only one of my friends knows about the way I felt about his sister.

It's the kind of thing that is likely to end a friendship.

When I experienced the feelings I described, I was in my 20s feelings things for childless 20 something women.

I would recommend not proceeding.

 

[davidsonj73]

Being timid at 18 is understandable.
Being timid at 62 is a condemnation.

Are you sure he wasn't smiling cause he thinks your into him or something, like homie knows you like women, right?

Like, what has compelled you to offer her son marital arts training instead of herself? This is the perfect activity to show off your skill and escalate, yet your choosing to steer away?

This post is so outlandish it's almost too obvious of a troll to be a genuine troll

I THINK he knows that I only like women. I would be willing to teach her and/or her son martial arts. I'm not a troll.

 

[davidsonj73]

It's a normal feeling to want to have sex with a male friend's sister. I have had that feeling on at least 2 occasions since I became a legal adult. I never acted on it. Only one of my friends knows about the way I felt about his sister.

It's the kind of thing that is likely to end a friendship.

When I experienced the feelings I described, I was in my 20s feelings things for childless 20 something women.

I would recommend not proceeding.

Ok. I won't proceed. I can imagine that even if he's ok with me being with his sister, if things don't work out with me and his sister, I will have lost a friend and perhaps made an enemy. I find it interesting that you and others think it's a bad idea to try to get with a friend's sister since my dad was friends with and attended the same synagogue as this guy named John, and John's sister and my dad met, started dating, got married and had me. They stayed married the rest of their lives. I think it matters VERY MUCH that John was ok with my dad dating and being with his sister. Maybe I should ask my friend if he would be ok with me dating his sister? Since he is a friend I would only pursue a committed/exclusive relationship with her, not a fling or for regular sex only. Wouldn't he probably tell me what he thinks of that idea if I ask him? And, if he doesn't like the idea, I'll say: "Sorry for bringing it up, I won't pursue it", and then change the subject. What do you think of that idea? She's a 9/10, otherwise, I would give up easier.

 

[corrector]

Ok. I won't proceed. I can imagine that even if he's ok with me being with his sister, if things don't work out with me and his sister, I will have lost a friend and perhaps made an enemy. I find it interesting that you and others think it's a bad idea to try to get with a friend's sister since my dad was friends with and attended the same synagogue as this guy named John, and John's sister and my dad met, started dating, got married and had me. They stayed married the rest of their lives. I think it matters VERY MUCH that John was ok with my dad dating and being with his sister. Maybe I should ask my friend if he would be ok with me dating his sister? Since he is a friend I would only pursue a committed/exclusive relationship with her, not a fling or for regular sex only. Wouldn't he probably tell me what he thinks of that idea if I ask him? And, if he doesn't like the idea, I'll say: "Sorry for bringing it up, I won't pursue it", and then change the subject. What do you think of that idea? She's a 9/10, otherwise, I would give up easier.

I noticed @Desdinova has not weighed in on the topic.

I'm going to chime in. Pursue the sister. You have no competition for her, she's a 9/10 and you already have chemistry. Your dad is an example of how you came into being. Sometimes you just don't know where your future wife will come from. If there is a chance then even if you risk losing your friend wouldn't it have been worth it to see if she was the one then not ever know and live in regret you didn't make a move?

There is a tendency for people on here to look at ethics (ie if a woman is seeing someone, or in a relationship, or is so and so's friend/sister she is off limits) rather than seeing if you both are getting along and there is a chance for it to go somewhere. Suppose this is your future wife/gf, are you really going to let other people stand in the way? He'll be the best man for the wedding!

 

[BackInTheGame78]

Good luck with that one...most women in their 30s think 50 is old let alone 60.

 

[SW15]

I can imagine that even if he's ok with me being with his sister, if things don't work out with me and his sister, I will have lost a friend and perhaps made an enemy.

It's not an "if". It's a "when things don't work out with me and his sister".

You will lose a friend for sure.

This reeks of scarcity mentality. This is not what a guy with seduction ability would seriously consider. If she were childless and 20 something, it might warrant more consideration, but most guys are unable to get a 20 something by 35-44.

Maybe I should ask my friend if he would be ok with me dating his sister? Since he is a friend I would only pursue a committed/exclusive relationship with her, not a fling or for regular sex only. Wouldn't he probably tell me what he thinks of that idea if I ask him? And, if he doesn't like the idea, I'll say: "Sorry for bringing it up, I won't pursue it", and then change the subject. What do you think of that idea? She's a 9/10, otherwise, I would give up easier.

You can have open communication about it. Generally, most men aren't going to want their friends to date their sisters. It's complicated. That's even true in the blue pill world.

There is no 37 year old with children who is a 9/10. You're overrating her.

 

[davidsonj73]

You can have open communication about it.

I like that idea. I certainly won't proceed if he doesn't want me to, since I value our friendship.

 

[davidsonj73]

I am the OP. The reason I am reviving this thread is for the following reasons:
1. I am attracted to a friend's (I'll call him B) sister.
2. I found out from another friend (I'll call him G) that B wants to have sex with G's daughter. He told G so!
3. Does this mean B thinks anything goes, so maybe I can try to get with B's sister, and B might be OK with it?

 

[Pierce Manhammer]

The only thing we’re not mentioning here is the 600 pound gorilla sitting in the corner of the room. You’re in your 60s she’s in her 30s the chances that she wants your wrinkled nuts sack hover somewhere under one percent probability yet somehow you’re willing to risk your friendship with a man over this possibility, which is pretty much nil already?

Seriously brother think about it. You’d have to be very stylish, familiar with mid millennial jargon and culture, you’d have to look younger than you are by a good bit and frankly, you better have the body of a fit 30-year-old and chances are you don’t.

Just a thought.

 

[BaronOfHair]

The only thing we’re not mentioning here is the 600 pound gorilla sitting in the corner of the room. You’re in your 60s she’s in her 30s the chances that she wants your wrinkled nuts sack hover somewhere under one percent probability yet somehow you’re willing to risk your friendship with a man over this possibility, which is pretty much nil already?

Seriously brother think about it. You’d have to be very stylish, familiar with mid millennial jargon and culture, you’d have to look younger than you are by a good bit and frankly, you better have the body of a fit 30-year-old and chances are you don’t.

Just a thought.

Lots of 60 year olds in the modern world don't look in the least bit haggard. With great respect to The OP though: He's also posted a thread asking "What sort of neck chain should I buy? I plan on wearing it 24/7"

 

[oOh Nasty]

Lots of 60 year olds in the modern world don't look in the least bit haggard. With great respect to The OP though: He's also posted a thread asking "What sort of neck chain should I buy? I plan on wearing it 24/7"

When I first read OP's post having to do with wanting to read books on feminism so that he can impress a feminist, it was such a big WTF moment. But now, learning that he's in his 60s, I give him respect for being able to come onto this platform at his age and still try to learn. A few of my uncles who are now in their 60s could do well by discovering this site and trying to see what they could still learn. I figure most men at that age, upon first coming into contact with a site like this, would scoff at it immediately or agree with some things but write it off as being impractical at his stage in life and too late to change (for example, my married uncle could do well by having stronger frame with his wife so she doesn't keep disrespecting him). Dude probably came here wanting some quick and easy tips to scoring that hot piece of 30 year old ass, but hopefully in the end, he ends up really learning and understanding the true nature of women.

 

[BaronOfHair]

When I first read OP's post having to do with wanting to read books on feminism so that he can impress a feminist, it was such a big WTF moment. But now, learning that he's in his 60s, I give him respect for being able to come onto this platform at his age and still try to learn. A few of my uncles who are now in their 60s could do well by discovering this site and trying to see what they could still learn. I figure most men at that age, upon first coming into contact with a site like this, would scoff at it immediately or agree with some things but write it off as being impractical at his stage in life and too late to change (for example, my married uncle could do well by having stronger frame with his wife so she doesn't keep disrespecting him). Dude probably came here wanting some quick and easy tips to scoring that hot piece of 30 year old ass, but hopefully in the end, he ends up really learning and understanding the true nature of women.

Amen. I recall watching a couple of David DeAngelo's videos, and seeing many older guys in his audience. It's never too late to work on oneself. And this is a much healthier use of one's time and energy than what so many of our grandparents did for the last 3 decades of their lives.... Watching TV from 9AM-12AM, 365 days a year

 

[BackInTheGame78]

The only thing we’re not mentioning here is the 600 pound gorilla sitting in the corner of the room. You’re in your 60s she’s in her 30s the chances that she wants your wrinkled nuts sack hover somewhere under one percent probability yet somehow you’re willing to risk your friendship with a man over this possibility, which is pretty much nil already?

Seriously brother think about it. You’d have to be very stylish, familiar with mid millennial jargon and culture, you’d have to look younger than you are by a good bit and frankly, you better have the body of a fit 30-year-old and chances are you don’t.

Just a thought.

People delude themselves into believing all types of things...seems like OP is on this path.

 

[NealIRC]

Should also depend on how you can the guy are friends. And 2nd of all, if you do have sex with his sister, will she tell him about it? Women are usually discreet about these things?

And she's 37 living with her brother? Why is she single?

 

[SW15]

I recall watching a couple of David DeAngelo's videos, and seeing many older guys in his audience. It's never too late to work on oneself.

David DeAngelo was big from roughly 2000-2005. Old guys in 2000-2005 would have been some earlier Boomers (1946-1955 birth years) and maybe even some pre-Boomers. Silents and Boomers had an easier mating environment than later generations. Things got more difficult for Generation X, but Millennials (originally called Generation Y before that term fell out of favor) and Generation Z have had it the worst.

A 62 year old has some time left so it's a good idea to make the most of it. I'm an early Millennial in my early 40s and I'm starting to feel my own mortality. I didn't feel this as much in my early 30s. I mention my early 30s because I was a mature man by that point in life too.

I give him respect for being able to come onto this platform at his age and still try to learn.

I am impressed that you arrived on this forum in 2002 at 16 and are still using it in 2024.