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female
age
41-50,
anonymous
writes: Please no judging, my sibling has a friend who I fancy the only problem I have is the age difference I am 42 he is 25. He has admitted in the past he liked me and this has gone on for the last 8 years. A few year back he actually sat discussing with mutual friends how it could work out and they took it with a pinch of salt. He is very confident and not in a cocky way where as I am very shy. I don't think he is after anything serious which is fine hes young. I would be up for some fun but not to shout about it. I dont want abuse from people calling me a cradle snatcher and other names like that, we live in a small town and word can get round fast but very rarely see each other out and about. If I did decide to have some fun I'm not sure how to even bring the subject up , should I just leave him to it and not try anything
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male
reader, anonymous, writes (10 January 2020): I disagree with the others hands off advice. Life is too short.
"I'd like to have some fun" sounds like have some fun in bed. And why not. You say you are very shy -- so that's a little problem. Can you chat with him on Facebook on via email?
Years ago when I was 25 a young widow in her 40's -- in my complex -- would give me a sexy smile and talk about the weather in a 'you can have me' way and a slight dirty joke. We became FWB for 2 years.
A
female
reader, Youcannotbeserious  + ♥, writes (7 January 2020):
 Some men prefer slender women while others prefer women who carry a bit more weight. Some prefer blondes, others prefer brunettes. Some prefer younger women while others prefer older. Without knowing you or this guy, we can only guess as his motives. It could well be he is actually drawn to older women, hence why he is drawn to you, or perhaps he just happens to find YOU attractive.
Or, given his age when this ersatz love affair started (17/18), perhaps you felt "safe" to flirt with and fantasize about and "practice" on. Many teenagers go through a phase like this where they hone their social skills, usually fixating on someone who is unattainable in some way (usually someone a lot older, like a teacher). Perhaps that is how this started and he has never actually grown out of it?
The question is, why are YOU fixating on someone young enough to be your son? Nothing wrong in that as such but, as you rightly point out, you are at very different stages of life. It's interesting that, despite saying you are ok with something casual, you are actually looking well into the future and realizing that you would probably be unable to provide him with children if he wanted them in the future. You are obviously already seeing this as a possible long-term relationship, which doesn't appear to be what the young man is after or what you SAY you would be happy with.
Given that you live in a small community where gossip seems to spread easily, I think you need to bear in mind that, if you do start anything with this young man, word is very likely to get out. Even if you are very careful not to be seen together, someone will say something to someone at some point and it will snowball from there. I totally understand your desire not to be judged, but you know people WILL judge you and point the finger. Given the age difference, they will point it at YOU, not HIM. And yes, terms like the ones you don't wish to see on here are VERY likely to be bandied about. Once word is out, you will have absolutely no control over what is said or how people choose to interpret it.
Now another question is, how important is that to you? Given that you say you are shy, I suspect people pointing the finger and whispering about you would upset you. Some people could brazen it out but I suspect you might not be one of them.
The last thing I would say is that women need to feel loved to want sex. Given that this guy is probably only looking for casual fun (possibly even a notch on his bedpost denoting conquest of an older woman), I suspect it would not take long before you wanted more from the relationship. One of two things would happen: he would either run a mile because a serious long-term relationship was never in his plan, or he would decide he wanted to settle down with you, so then you would have your issue about being too old to have children.
It all sounds unnecessarily complicated to me. I'm not saying it is WRONG, because you are both single adults (I assume) so you should be free to do whatever you want. However, you yourself have thrown up lots of possible red flags. I think you need to think through the possible consequences. We can do anything we want in life but EVERYTHING comes with a price. What price do you think this young guy is worth?
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A
female
reader, anonymous, writes (7 January 2020): OP here. Didnt do anything with him 7/8 years ago because I felt it was wrong due to his age. My sibling and other mates never bat an eyelid when it was mentioned before. He has admitted to a few people he likes older women. I didn't expect him to get back in touch and want to go for a drink. Hes not a giddy and silly lad hes got a slightly older head on his shoulders. Reason I'm seeing this as a bit of fun is why would a young lad be interested in someone as old as me. He has had girlfriends his own age but dont last long. Also if in a few years time if he wanted children I can never give them as I'll be too old
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A
female
reader, Honeypie  + ♥, writes (7 January 2020):
 Besides the fact that it's been 8 years of knowing him and NADA!! has happened isn't that a clue? It was a few YEARS ago he thought something could happen, THAT is a LONG time for nothing to happen and he might have been blowing off steam with his friends, bragging that he could "land" an "older" woman or it might have been something he was curious about, yet... he never talked to you about it. Never suggested it to you.
And secondly, if you are JUST looking for fun, why on Earth would you go for a FRIEND of your sibling?
Let's say he turns you down, AWKWARD!
Let's say you get it on and you want more but he doesn't, AWKWARD! (it's EASY to say you are OK with him not wanting anything more but REALITY might be totally different, you won't know how you FEEL after the "fun".)
Let's say HE wants more but you discover that he really IS young and immature and NOT really someone you can see yourself with in a serious manner, AWKWARD!
As BAD as looking for dated at work, dating FRIENDS of a sibling is just plain NOT a good idea. Because you are not the only one where things can get AWKWARD!
Or even better TALK to your sibling, she what she/he says.
As for the age difference, 25 and 42? eh.. not a big deal. If you had pursued it 8 years ago when he was 17 and you 34.... I'd say gross. Because he wasn't of age. At age 25 he isn't exactly cradle/jail bait no more.
Also, is all you are looking for is "fun"? Why?
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A
female
reader, CarrieSoa +, writes (6 January 2020):
 You say that the mutual attraction has gone on for 8 years? From he was 17 and you were 34? That in it's self is worrying. You are 42 year old woman wanting to play with a young guy just for fun? It will not be just fun for you. Can you really handle having no strings attached sex with him while he sleeps with other women? I doubt it. It will eat away at your self esteem and you'll grow to resent him.
You start your post being defensive which means that you really are self conscious about how people will view an older woman sleeping with a younger guy. In all honesty, you are an adult, he's an adult so why should you care what other people think?
When it comes to matter of the heart you have to be prepared. Women cannot have sex just for fun. A chemical is released in a woman's brain when she has sex with a man. This caused her to emotionally attach and cause her to feel love for the guy. It may be temporary or it may not be but this is what will make you feel hurt when he sleeps with other woman.
I Would avoid any sexual involvement with this guy.
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