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male
age
51-59,
anonymous
writes: There’s a young lady that I have an interest in. It’s not a sexual thing, really. I can’t explain it, there’s just something about her that makes me want to get to know her. The first issue is I’m forty and she’s twenty. Although I’m a young at heart forty year old, I still worry it’s a bit weird.The second issue is I don’t really know her personally. I haven’t laid eyes on her for a year or more, and when I did see her regularly we never really spoke but I think she might have had a crush on me, or was at least interested in some way.Ok, here’s where it gets weird... I knew her when I worked at her school when she was in her late teens. I used to work there as a cleaner. Although she spoke to me a couple of times and I caught her looking at me a few times I never approached her or tried to get to know her because I was worried that it would be inappropriate.But the thing is I find she’s on my mind a lot. I stumbled across some videos of her on You Tube, just goofing off with her friends, and it’s given me a feeling of sadness, of what might have been if we’d have become friends.I’d like to make it clear I don’t make a habit of having crushes on teen girls. I haven’t felt like this with any of the other students. I’m not sure it’s even a crush. I’m always professional at work. I don’t approach students or to talk to them. And it’s not like I’m lusting after her. There’s just something about her that makes me wish I could get to know her.I’m single, have been for a long time and yearn for a relationship. I also don’t have many friends and I get very lonely. I could really use a friend. And there’s also a regret at letting the opportunities to get to know her slip away. On two occasions she spoke to me in a friendly manner and I had the opportunity to chat and get to know her but I didn’t. And that grips me with such sadness.So ok, the reason I’m writing all this is because I know she has a Myspace page and I wondered about contacting her to say hello. I don’t know if she remembers me or if she was interested in me or not. I don’t know how she will react to hearing from me. Will she think it’s weird? The last thing I want to do is to make her uncomfortable. I’d keep it really casual, just “hi, remember me? How’ve you been?” And I’d most certainly drop it if she didn’t reply. I wouldn’t try again. The last time I saw her was about a year ago at the mall. She walked past with some of her friends and I’m almost sure she looked over at me and recognised me.I’m aware that I should drop this and forget about her. And I don’t plan to contact her unless all of you tell me its ok (she is an adult now after all). But I keep wondering what if she really liked me, and still rememberes me, and would love to hear from me? It’s the thought of what might have been and what I might be missing out on that’s gnawing at me. And by that I mean friendship with a really awesome person. So is this wrong? What should I do? Ideally what I should do is meet someone my own age and forget about all this but I don’t meet women. I’m very likeable and easy to get on with, it’s just I don’t know how to go about meeting them. Plus I’m a bit on the shy side and have had some bad luck in the past.Like I said I don’t plan on doing anything, and I won’t do anything unless you all say it would be ok and I should go for it. What do you think?Thank you.
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male
reader, oldnavyht3  +, writes (17 January 2011):
Dude it's perfectly okay to feel this way. For years kings and lords have had friendships, marriages with women half their age, Its commonplace and society accepts older men with younger women. I'm forty about to be forty one and I find myself as well looking and hanging around women in their twenties and form asking around most women love an older guy versus a younger guy.Think about it, the first man in a woman's life is their father, an older man who is mature, securing, loving and so as an adult they look for those qualities in a relationship and who do you think they look for... the prize... an older man who is mature, loving, responsible, and will treat her with the loving, understanding and most importantly the "attention" that daddy did when they were growing up. Its like a windows program in them they instantly have this inside urge to be with an older man being that most younger guys are out to have fun, enjoy life, and are not really interested in settling down unless the iron fist of family presses them to do so.SO enjoy yourself don't feel guilty, when someone asks how old are you tell them old enough to know better and young enough to enjoy it.
A
male
reader, anonymous, writes (28 July 2010): Hi, OP here.
I sent her an email but it's not looking good. I didn't send it to her Myspace after all because I noticed she hadn't logged on in a month. But it has a link to a local amateur radio station she's involved with. I had a look at the website and she has her own email address there so I figured it would be smarter to email her there instead. I could use her work with the radio station as an ice breaker as well.
I did the whole "Hi, you probably don't remember me blah blah, how're you doin blah blah, take care." thing as suggested, keeping it light, not in any way pushy. But it's been a few days and no response. I know she checks that address because I decided to ascertain if she did by sending an email enquiring about the radio show she does without telling her who I was. She replied to that quite promptly and she sounds friendly so I'm a bit surprised not to even get a hello.
I may have put her off slightly because I actually sent the first email (the one just enquiring innocently about the show) twice, once to the stations general address and once to hers. The weird thing is I used my first name and private email for one, and my middle name and hotmail address for the other. She's bound to realise they're from the same person and might be suspicious as to why the names are different. I have no idea why I did this. None at all. All I can remember is it made perfect sense at the time. Ah well.
So I guess that's it. I tell myself that at least I tried and I'm no longer tormented by thoughts of "What if? What if she really liked me and would love to hear from me and all I'd have to do was contact her somehow?" Now I know that's not the case. I'm beginning to wonder if I imagined the times she spoke to me and the little looks. I feel a little stupid actually. I guess I should learn a lesson not to see significance where there is none.
Thanks again for the advice and understanding.
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A
male
reader, anonymous, writes (19 July 2010): if you do become friends ok. if it leads to something else realize that she is younger and proably wanting to sow some wild oats, so don't be surprised if she goes out looking for "strange"
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A
female
reader, anonymous, writes (19 July 2010): Go for it !. My mum was 17 when she met my dad, and he was 33, and they were together for 28 years !!. I also have a half brother who is 44 and he is engaged to a woman who is 27 !. I am also interested in someone 20 years older than me . I'm 26. So, age gaps seem to run in my family a bit lol . Life's too short to worry about what other people will think of the age gap, and you only live once, so you dont want to have any regrets, do you ?. If she really did keep looking at you, spoke to you ina friendly way, e.t.c, it sounds like she could like you.
About the man i like, i was only 21 when i first met him, and he was 41. I must admit, i felt quite intimated by him at first, as no one who was so much older than me had ever been interested in me before. He has also been single for a long time, he has never been married. I dont know how many relationships he has had, but i know he did some things in the past that some people think are bad, like going with women just for sex, but apparently, it was a long time ago. Some people we knew said some horrible things when they first knew we were interested in each other , such as " why is she hanging around with him ? " and " what is he doing hanging around with that young woman ? " . I think it bothered him more than it did me, and he asked me what i thought of the age gap, and he said he thinks a lot of me, but he's sick of people sticking their noses in.
He also winks at me a lot whenever he sees me, everytime i see him. I never see him do that to anyone else.And he makes me laugh. Other times though, he has been distant with me. So, sometimes it can be complicated when there is an age gap. So basically, i have known him for five years, and we did have a few dates, but at the moment, i'm not sure what he wants, although, recently he saw me out with my father, and he told me that he wanted me to introduce him to him, because he had never met my dad before, and i have also met his parents, and his siblings. He has been a friend of some of my family members for years, although, a couple of them think he is too worldly for me, so i guess that is another reason why he might feel funny about having feelings for me too.
I guess the main thing is, as long as you are genuine about this woman and honest and trustworthy, and don't listen to other people's opinions too much, it could work out ok. This may be the first time that a much older man has taken interest in her too, so, as others have said, i think you should write to her on myspace, and keep it light and casual at first, then , if you get the feeling that she likes you, maybe you could try some online flirting, like adding in emotion symbols, such as smiling, winking, or by making jokes, e.t.c, or, you could save the flirting until you meet up . Then, eventually, you can ask her if she wants to go on a date with you. I hope this helps. Good luck, and please keep us posted !.
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A
female
reader, Denise32 +, writes (19 July 2010):
 I'm with Bernard on this one. It won't do any harm to drop her a friendly line, remind her who you are, and ask how she's doing and does she remember you. Be friendly, yet casual, and see if she responds.
If she does, great, you can make arrangements to meet for lunch or coffee, perhaps after a couple more emails, and see how it goes.
If no response, then it would be a good idea for you to try getting out and about more, places where you might meet other women, or even a dating site or two.....good luck!
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A
male
reader, anonymous, writes (19 July 2010): dude you need to get out a little bit. yeah you are taking it the wrong way, dont take this wrong, just she is being normal and you are reading to much into it. find someone your own age and you will be happier
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