A
male
age
51-59,
anonymous
writes:I am 40 year old single male. I live in a duplex.My neighbor is a 21 year old very attractive female.She is sassy, fun, and spontaneous. She doesnt have a washer and dryer, so this is how we started to get acquainted. We have a good friendship. I cook for her do errands we watch movies play games, talk etc...Problem is I am starting to have strong feelings for this girl. She spends more time in my place than her own. She says she is not into older guys. She likes the 20 somethings. I am little confused with what to do and how to proceed. In my mind having had a few relationships we get along really well and I enjoy spending time with her, but I am wanting more fom her.She has a few male friends and I have found myself feeling jealous lately.I feel like I am in a no win situation. If I confess I really like her and want to be with her I think she will cut me off. Yet, to be around her and not be able to express myself I dont know if I can do that either. What is the best thing to do?
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male
reader, The old Man? +, writes (1 February 2009):
 I don't think you're being far fetched at all! The inter generational dating thing in the USA is recently becoming more common.
You say that she spends more time at your place than she does at her own, you cook for her, run errands, etc...
I think the real issue you need to address is, Does she have genuine feelings for you? Or does she realize that she is an attractive young woman, and you are an older man who is attracted to her. In turn, playing upon your emotions and having you do things for her?
Young immature women have been known to use older men!
It could go either way. Just because she says that she would NEVER date an older man, doesn't necessarily mean she'd never date an older man!
Never say NEVER!
You hear them make their negative comments about older men. You know, "wrinkly old man etc.." Often times, they are merely repeating the words that they have heard their friends say, yet never experienced how we treat them, and we're actually quite capable of showing them a better time than our younger counterparts!
It is possible that it hasn't sunk in on her the things you do!
Perhaps cut back a little, and not be so willing to offer. When she asks why, in an effort to not ruin the "friendship", make it a mild joke. Say something like "I normally only do these things for a girlfriend, or someone that I am dating, and being that you wouldn't consider dating me, I probably shouldn't be treating you as such."
That will leave things open for her to reply, or just think about.
I have dated a few women in their 20's. One of which was one of those who said she'd never do that. She's the one who gave me a buddy slug on the shoulder and said: "Ya know, you're pretty cool old man, I really like you"! We saw each other for a good long stretch!
I hope this helps!
Feel free to e mail me.
Joe~
A
male
reader, anonymous, writes (31 January 2009): I have always dated women my own age within 5 years on either side. I have never thought about pursuing someone who is 15+ years younger than me. I did not start hanging out with her she started hanging out with me. I know how I was at 21 ya totally green and a know it all. Anyway, never imagined myself in this situation. So, if anyone else responds don't be so quick to judge. Life happens.
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A
female
reader, anonymous, writes (31 January 2009): Sorry but she's already given you a warning. She told you, I don't date older men. That was a massive hint. Now, you need to get over her and move on because she's not gonna go there with you.
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A
male
reader, eddie  +, writes (31 January 2009):
 I'm 45. I have a daughter who is almost 20. I actually had this conversation with a single 45 year old male friend last night. He tends to like younger women. I find it creepy.
People who are 20 think they know a lot. They usually don't. They can survive on their own but they are very green about life. I think it's an unfair situation. My buddy thinks I'm wrong but I remind him that he has a 5 year old daughter and I'd like to see how he reacts in 15 years when some middle aged dude is trying to get with her.
As a man, you see her as an attractive young lady. You are having feelings for her. She has told you she is not into older guys. That is a very clear statement. Take it as a message that she likes your company as a buddy.
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A
male
reader, 24yeahright  +, writes (31 January 2009):
Dude. You need to just come out and tell her.That jealousy will consume you. Whether it's intentional or not, she's screwing with your head.Just do it man. DO IT.
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