Jared writes, “I’m a 30 year old guy and have for as long as I can remember been attracted to my mother’s best friend. She is in her 50′s. I’ve always dated women older than me, and this woman knows it – she knows also that I’ve fancied her for about 20 years! A year or so ago – I decided to take a step out of my comfort zone and began making it clear to this woman that I’m not 10 anymore and I want her. My worst fear was that she would relay my messages to my mother – which needless to say, would have been most embarrassing. But she didn’t. My messages were about as blunt as you can imagine! At the time of sending the texts she didn’t seem at all surprised or in fact disturbed – but at the same time she didn’t confess to having similar feelings (frustratingly!). She quite literally said nothing, so since then I’ve periodically continued to make my feelings clear whenever an opportunity has arisen. I realized, however, shortly after my initial texts our friendship dynamics had changed. Her tone was different when talking to me – it was a nice change. Like we were sharing a secret from the people around us. She’s not in a relationship and while I don’t doubt we would ever have any sort of conventional relationship – this woman is my all time fantasy, all the way from a teen to a grownup man. she looks young for her age and has a body many twenty something’s would give their right arm for. I really want this woman. My question to you and your readers is how can I put this to bed (pun intended) once and for all?”
Well, you have done everything that you needed to do in order to make it clear to her what you want. The fact that she has not recoiled in horror, chided you for misbehaving, and spoken to her best friend about you clearly means that she likes the attention.
I do not think that you need to do anything more than just wait. She is a grownup woman who knows what to do if she wants to have sex with you. At this point the ball is in her court and you just have to wait like a gentleman in the meantime by trying to be sweet to her, flirting with her, and maintaining a relationship by text and conversations when you meet. If she has not already acted on your fantasies, it could be for a variety of reasons:
- She has not found the right opportunity.
- She is afraid that if she is caught she might lose her best friend forever.
- While she likes the attention, she is either not attracted enough to you to have sex or maybe has a relationship with someone else that you may not be aware of.
- Since she does not see a future with you, she does not think that having casual sex will do any good and may not be worth the risk.
- She feels guilty about sleeping with a man whom she looked at as a son at some point in her life. Trust me, it ain’t easy for someone older.