A
male
age
30-35,
anonymous
writes:My long time friend is getting married and asked me to be the best man in his wedding. He will be marrying in a few months after he graduates from university. He and I have been friends for a long time and have been attending the same university and graduating together. Besides being the best man I asked if he and his future bride needed any help planning the wedding and they said that they might. They invited me over to several planning time.It has been nice helping my friend plan the wedding. I have also gotten the chance to see the mother of the bride more. I have been introduced to her in the past however planning the wedding with her, her daughter, my friend, and his folks I have gotten to spend more time with her. She has been divorced for about a year. She is a florist and is very artistic and striking. She is an Italian woman and I have a thing for Italian women. I have heard that Italian women make great lovers. Is that true? During the last wedding meeting she asked if her daughter would like to go with her and help her pick out the dress for the wedding. Her daughter said that she had too many other things to do without that. I offered to go with her and help her choose the dress. She said great. We had a fun time looking at stores and talking. She would change into dresses and model for me. I would tell her what I thought and always made a nice comment. She found a dress. After that we had lunch together. We enjoy our time talking together. After it was over when it was time to split up she thanked me for going shopping with her and for lunch. She said she had fun and I said I also had a good time. She then gave me a nice kiss on the cheek. I did not know what to think of the kiss. It may be cultural for Italian women to greet with a kiss. I mentioned that it would be fun to have dinner together. She said that it would be nice. She said that since I was so nice that she would cook a dinner for me.I would like to become more intimate with this woman. How can this be done? I came over to her house for the dinner and it was great. The food and the company was great. I did not put any moves on her. I did not want her to think that I came with a different intention. When I went to leave she gave me a nice kiss on the cheek. This makes me think it is cultural. That night I dreamed about us being together. I would like to spend more time with her. Perhaps I will have a chance to dance with her at the wedding but I hope I can see her before.I would really like to have sex with this beautiful woman. How can I let her know that I am interested in sex? And particularly sex with her? Would telling her about my thing for Italian women help? Should I tell her about my dream the other night of us being together? Do you think there is a chance given the fact of the difference in our ages and the fact that I am in the wedding and friend of her daughter’s husband?I am thinking that an ideal time to make it with her is after the wedding when her daughter and my friend are on their honeymoon. I want it to be a special time for her. I am also wondering whether she would like it in her house or it would be more enjoyable to take her on a mini trip for a few night together. The mini trip would allow for her and I to spend time together other places. Any thoughts on this?
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, Youcannotbeserious + ♥, writes (4 February 2022):
 So all you are after from her is a bit of sex? I'm sure she would be really flattered to know that.
Do her a favour and leave her be. She deserves someone who is looking to have a committed relationship with her, for whom sex will just be a part of the bigger picture and a natural progression from friendship, companionship and, ultimately, love.
A
male
reader, anonymous, writes (3 February 2022): I agree with Honeypies view that it is a bit unorthodox dating your best friends MIL but on the other hand as the saying goes,faint heart never won fair lady. My suggestion for the time being put the sex part completely out of your mind and be genuinely friendly with her and when your friend and his bride go on their honeymoon invite her to dinner as a return to her dinner invitation maybe after that you will have a fairly clear opinion if she is willing to go further but FGS just keep sex out of it for the time being and don't be a letcher be a gentleman let things take its course.
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A
reader, anonymous, writes (3 February 2022): This particular topic is loosely based on MILF porn. A woman is a woman, and if a guy likes a single and available woman, he'll figure-out how to meet and to get to know her. Having a "thing" for some specific "type" of human being (based on stereotypes) almost relates to ethnic-fetishism. See women as intelligent, feeling, mysterious, and one of God's greatest creations. Not something to be objectified and used for pleasure and discarded. Dear Cupid is inundated with posts from women just trying to find (or keep) a guy who truly loves them, and will treat them right.
Funny, few men ever write DC and ask about how they can commit to a woman, establish a long-term relationship, start a family, and be true to the one lady who loves you. Not this nonsense about how to seduce and boink an old-woman. If that's what a guy wants, he'll get it. If that what she wants, she'll find a way to get it.
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A
female
reader, Honeypie  + ♥, writes (3 February 2022):
 Dude!
She is your BEST friend's MOTHER IN LAW! Keep it in your pants.
I don't know what it is with guys who think all divorcees are looking for a younger man to just have some sex with! This is the second or third question this week with a similar story.
The kissing on the cheek, well I know a lot of British people, a lot of Danish people who do this too among friends. So it's not something "strange" that only Italian people do, but you DEFINITELY see this in France, Italy, Spain, and Portugal.
You are thinking with your dick. Aren't YOU a little too old for that? You have already thought of WHERE to have this sex, her house, or a mini vacation, like THAT is what SHE is looking for! She isn't some two-bit actor in your private MILF porn movie
Maybe she just enjoyed the attention and company while dress shopping. That doesn't mean SHE wants to sleep with you.
Think a little. Is it even appropriate for you to chase after your BEST friend's MIL?
Are YOU so hard up that you can't find someone to date? So you go chase after random ladies that are related to friends? Who's next? Your BEST friend's mom?
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A
reader, anonymous, writes (3 February 2022): The idea that all Italian women are sexy is ridiculous. As with any nationality some are some are not, it will also depend on the man. If the man is a soppy child she won't be sexy with him. You forget that sexy desirable women get a lot of guys chancing their arm with them and can pick and choose. You would have to be more worthy and special than the others to be taken seriously. Other than sex what can you offer her - she can get that in bucket loads, it's guys who struggle to get it. What makes you worth considering as a lover? This idea that you will just have a few days or hours of sex is ridiculous. You talk as if she is a sex worker who is just there to pleasure horny men. Older sexy women want a lot more from their man than just sex and chat. Have you got a good job, are you charming and smart, are you well dressed, good looking, own house, nice car. She can easily get a man like that if that is what she wants. In the meantime if you want to go with an older woman who is sexy pay one.
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