Q&A: I’m 20 and Want To Date A 65 Year Old Woman

grandmaI’m a 20 year-old guy who’s a virgin, but who’s known this older (like around 64-65 years old) woman all my life. She’s still sexually attractive for her age, and I wouldn’t mind getting in a relationship with her. I figure that it could be beneficial for both of us: I could get some experience with a woman who’s had sex before, and she could A.) get some hopefully decent sex (since I doubt she’s gotten any in years) and B.) know that she’s still desirable. Plus, I figure there would be little to no chance of pregnancy or STDs, since she’s post-menopausal and I don’t think either of us have been able to pick up any bugs recently. The relationship probably wouldn’t last for very long (hence my calling it a “fling”), but that doesn’t mean it wouldn’t be worth a go.

However, just because I’m interested, doesn’t necessarily mean she is. She has rather Victorian view on sex and relationships, and we’d have to get around that before anything could happen. It’s not that she’s religiously conservative; she’s just old-fashioned.  She doesn’t know what to think of homosexuality or transgender people (her attitude is often slightly negative on those subjects), and she doesn’t seem to approve of relationships where there’s a large age gap. However, in a short-term relationship like this, the only disadvantage I can think of in regards to age gaps is if the older partner is taking advantage of the younger one, and I don’t think that would happen here. (Since I’d likely be the one initiating the relationship, and since she’s kinda meek in general.) Plus, she’s post-menopausal (I’ve heard that menopause can kill a lady’s sex drive) and on antidepressants (which I’ve heard can also kill sex drive). Even with the antidepressants, she’s got low self-esteem, so that combined with her age may make it so that it may not even occur to her that anyone can be sexually attracted to her. Plus, she’s married. I don’t think infidelity would be her greatest concern, but it would be on her mind.

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