52 and never been kissed

I'm 52 and I've never had a girlfriend. This isn't because I'm gay. I've always liked girls/women. It's partly because my life has been a bit unusual, and partly because I am an awkward and cautious person who doesn't rush into things. I was an only child, and my mother, though very caring, was over-protective. She encouraged me to feign illness and stay off school and then work for nearly six years so I had very little contact with people my own age and no contact at all with girls. I finally got back into work at the age of 22. Although I had broken away in part from my mother's protectiveness, I continued to live at home. I was always short of money because I gave most of my wages to my mother, so I didn't have enough to ask young women out, and in any case, I found it very difficult to make friends with them. I didn't start going for nights out until I was 28. I was never cheeky or forward with women. I would just ask them for dances or try to talk to them politely, but all I usually got from them was rejection or dirty looks. In eight years of Saturday nights out, I only got about 3 dances with girls and only got friendly enough with one to ask her out. Even she turned me down. All this eventually destroyed my confidence, and I stopped going out regularly. In other situations where I tried to make friends with women I found attractive, such as work or college, I had the same rejection or dirty looks. On several occasions, I was messed about by women. They'd stand me up or smile and be friendly towards me, then sudden become cold or standoffish when I tried to talk to them. I don't know why women have treated me like this over the years. It doesn't seem fair, because I've always had great respect for women, never looked at porn, never wolf-whistled, been suggestive or discussed them in crude or derogatory ways, never tried to rush any woman into bed or dreamed of being unfaithful. I've never had many friends or gone on nights out with the boys, so I would have been totally loyal to any girlfriend or wife and given her all the devotion and affection possible. Some men have done all that yet never seemed to have problems finding women, sometimes really glamorous ones. Perhaps if I'd been more like them I might have had a few girlfriends by now, but being like that is just not me. I've been in love three times, at 15 and 19 with girls who lived nearby. I didn't know either of them personally. I never even spoke to them. When I was 24 I got to know a girl in the same office. I asked her out and she initially said yes but got cold feet. I chased her, which I've never done before or since, but she kept turning me down. Eventually I made a fool of myself by sending her a stupid Valentine that made it too obvious who I was. It put her on the spot and we never really spoke to each other properly again. I still think about her. To be fair, I have had a few chances to start relationships with women, but the awkward and cautious side of my nature has held me back. In my mid 30's I worked with a very attractive teenage girl. We got on well and she dropped heavy hints that she liked me, but she could swear and be grumpy at times, and that put me off her. Later a temp and I went out a couple of times and got on well but she was seeing someone, and I didn't want to try and break up her relationship. A few years back I got friendly with another woman but I found out she was quite weird in some ways so I backed off. I've never been the sort of man who'd just go for any woman who was available. I have to be attracted to someone and feel comfortable about everything with them before I commit myself. I have no idea of whether or not women find me attractive nowadays. I used to get told I had film-star looks by older women but women my own age showed no interest in me. I'm reasonably fit as I look after myself but my face looks too serious or gruff and I'm thinning on top. Because of my age and looks, and my experiences, I don't try to talk to women any more. I don't want dirty looks or rejection that will make me feel stressed and uneasy. And I don't trust women any more in case they're just playing games. I'm not lonely though I live alone. I'm not seething with desire, but it would just be nice to have a girlfriend. I could go on a dating site, but it's not really what I want because it's staged and artificial. Why can't I just make friends with women naturally so I'll have more opportunities to ask out any that I find attractive? D

Dear D

As you wrote your letter, I wonder if you saw all the ways you've been blocking yourself? You've put girls/women on a pedestal and been afraid to approach them, even kidding yourself love is possible when you haven't exchanged a word. You've tried to hand women the burden of "making" you happy. When a woman's smiled at you, you've read a whole lot into it that wasn't there. When a woman's turned you down, you've got stressed by telling yourself you're unattractive, unworthy and unlovable. Because some women are game-players, you've conned yourself into thinking they all are. You've avoided most of the usual ways of meeting women: networking, group activities and nights out, almost certainly because you you were so focussed on rejection that you came across awkward and desperate. As if all those obstacles weren't enough, you've made things even harder for yourself by being judgmental and stand-offish. Sorry to be so blunt but you need to know. You also need to know this isn't about who you are, it's about what you do. And that's something you can change - if you want to.

You can't judge a book by its cover and you can't tell whether any woman will suit you until you ask her out. Asking people out isn't a commitment. It's a numbers game. You have to be in it to win it, and everyone strikes out quite a lot while they're practising. Just as you might like fish and chips and others might like curry, that doesn't mean there's anything wrong with you or them. Nobody's universally popular. Your worth doesn't depend on the taste of some random woman (or women!). There's somebody out there for everybody, including you. But you have to kiss a lot of frogs before you find your princess. And you have to practise being yourself around women and not idolising them, so a few casual dates are just what the doctor ordered.

Assuming you're clean and presentable, you might try updating your image so you don't look fuddy-duddy or stuck in the past. Then I invite you to join things. Adult education classes, interest groups, singles groups, a confidence or assertiveness class. Practise talking to men and to women. Learn the arts of friendship with boht sexes, because women are just people, some you'd like and some you wouldn't, and vice versa. A girlfriend is a friend who is also a girl. Don't keep blaming the past. That's not where you live any more. What's happening now is about what you do now. Practise saying to yourself, "I enjoy being a vibrant, attractive guy." And start living in ways that show it to yourself and others.

Don't forget, other women are not your mother. They're not all-powerful, and you're not a kid. Do you really need to keep that glass bubble between you and the rest of the world? I wish you luck, D.