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Interested in an older woman... how can I find out more about her past sex life?

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Question - (4 March 2009) 4 Answers - (Newest, 4 March 2009)
A male age 26-29, anonymous writes:

I have been friends with an older woman for a while now. I am interested in moving out of the friendship zone and become lovers with her. How should I let her know this? Any tips for telling her this?

She is what I call a “beautiful” woman. She works out and her body looks hot. I tend to think that “beautiful” women get more chances for sex. Is this true?

Before becoming lovers with my “beautiful” woman I think I would like to know about her sex life. I wonder how many times/ partners she has had sex with. I am also interested to learn what she likes sexually. How can I find out these things? Any tips?

View related questions: her past, sex life

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A female reader, Tisha-1 United States + , writes (4 March 2009):

Tisha-1 agony auntHow to let her know you're interested in her as more than a friend? Ask her out on a proper date, a romantic restaurant, a picnic that you prepare, a show followed by a late supper. Whatever you choose, make it obvious it is a date-date, not a friendly hang out thing.

She will then know what you are asking her, and then she can make her decision to accept or not accordingly. Don't take a 'no' too personally; it may just be a function of your age, and not a reflection on the man you are.

You do NOT ask her about her previous sex life, nor do you talk about sexual techniques. The way you put the question, it sounds like you are more interested in it in a voyeuristic sort of way, and that is just kind of ooky. She's an older beautiful woman, chances are she has had some kind of sexual past, why not simply go with that assumption and leave the details for when you two are thinking of becoming engaged.

What she likes sexually is what you find out on your own with her, if you get that far. No shortcuts for you, young man, you need to do your own homework. First, find out if she'll even go out with you. The rest is moot if she won't.

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A female reader, DrPsych United Kingdom +, writes (4 March 2009):

DrPsych agony auntI appreciate you are quite young, but do you actually really like this friend or is she just a good looking fling for you? I don't know if your reasoning is right - beauty is in the eye of the beholder and is not an index of sexual partners. However if you ask her, she will run away...well probably, many women wouldn't be too pleased to be screened in this way. My advice is to forget about her past, why should it matter (feeling insecure about her comparing you to others?).

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A male reader, Griffo Australia +, writes (4 March 2009):

Griffo agony auntYep don't ask. One of the top rules: never ask a woman about her past.

Just go with the flow and don't let it blow.

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A male reader, mulattoman United States +, writes (4 March 2009):

mulattoman agony auntYeah here's a tip. Don't ask. She will be completley turned off by you butting into her past sex life. She would feel like you'd start judging her based on her past. Do yourself a favor, take my advice, and let it remain a secret.

If you two persue a relationship, make it well known you expect her to be honest about what she does decide to tell you, and to inform you which of her friends she's had a past with. That's the least amount of respect you deserve if you get sexually involved with her.

Sometimes I wish I didn't know all the things I do about my girlfriend. It made me feel jealous and unworthy all the time. At the same time It's good to know SOME things. But not all things.........

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