Ask Lynn-I’m 55 And Never Had A Girlfriend

His shyness and nerves around women kept this lifelong bachelor from pursuing women romantically, but at 55, he questions the idea of spending the rest of his life alone. Lynn offers some wise advice.

By Lynn Harris

ear Lynn,
I haven't registered for online dating yet, but I have been working on a profile and I have a photo picked out. The reason I haven't registered is because I'm in a rather odd situation. I'm a 55-year-old male that has never been married. Now, here's
This change in my life made me think about my relationship status.
the odd part: I also have never had a girlfriend and have been on only one date in my life. Part of the reason why is because from my teens up to almost age 30, I was very shy around women. As you can imagine, when I thought of asking a girl on a date, I froze with fear. I did overcome my shyness, but by then, I had settled into a lifestyle that I was very comfortable with. I had a job that I enjoyed, good friends, a social life, and I was involved in activities that I found challenging and rewarding. The idea of getting into a relationship simply became nonexistent. That was something other people did. I was happy with my life.

But a couple of years ago, things started to change. I suffered a couple of permanent injuries that now prevent me from doing some of the activities that I truly enjoyed. I came to the realization that those activities were a big part of my life — and now they're gone. I'm not physically disabled in any way. If you met me in person, you would think I was perfectly normal. It's that those activities were physically demanding and my doctors told me not to do them anymore. This change in my life made me think about my relationship status. Did I want to spend my entire life alone? The answer keeps coming up: no. Thus, I had the idea of registering for online dating.

If I do find someone, how do I handle telling her about my past? What would a woman think of someone like me?
– Really Late Bloomer

Dear RLB,
You know, I think they say that 55 is the new 40 (or something like that). In other words, though yes, you may feel late, you are by no means too late! Look back at the major changes you've already made as an adult. They may have been slow in coming, but they happened.

Also, your "past" may be unusual, but it's not that weird, or difficult to shift away from. I mean, think about it: most advice-givers (rightly) tell folks looking to share their lives with others to make sure their own lives are in order first. The latter, it should be noted, is the hard part, and you've done it. You overcame a major obstacle (one that some never do), found a job you loved, made good friends, and discovered activities that spoke to your soul.

Further, when someone is usually hesitant to reveal their past, it's because of stuff they did they're not happy about. You don't have
Talk about it, but don't make it a Big Huge Giant Deal.
that problem! Your slate is perfectly clean.

So how should you out yourself, then? Talk about it, but don't make it a Big Huge Giant Deal. When you've been out a couple of times on dates and start to feel comfortable — and know you want to go out a few more times — say something like, "You know, one of the reasons I'm really enjoying spending time with you is that this is all kind of new for me. I'm pretty inexperienced with dating and relationships. I hope you'll bear with me." The right woman — or at least, a woman who could be right for you — will understand. Don't over-think it or underplay your skills. Some people have a lot of dating experience and are still clumsy at it.

That said, let's not ignore the elephant in the room — the one with the big, shiny rhinestone necklace in the shape of the word "virgin." You didn't specify, but I'm guessing this is also part of your back story. Again, it's statistically unusual, but not insurmountable. For every, let's say, nine women who might find it weird, there may be at least one who thinks it's atypical but preferable to other weird things she's encountered, one who'll find it refreshing, one who is stoked because she's had limited experience herself, and maybe even one who finds it to be hot. We all have our deal-breakers and deal-makers, and sometimes we revise them based on the people we meet. You never know!

One other thing to consider: you might be asexual, and if so, that's fine! Lots of people are (and lots of those people are here: For the record, asexual people — who are, to put it scientifically, basically just "meh" about sex — can live full and happily fulfilling lives, often in romantic or otherwise more-than-just-friends relationships. Maybe I'm way off-base (or maybe you're not interested in this kind of self-evaluation), but it could be illuminating. It could even give you another way to meet someone who shares your interests (and/or lack thereof, if you know what I mean).

Anyway! Not everyone needs a relationship (or sex, for that matter) to be happy. So you're not required to have one (or it). But yes, you're entitled to find someone, if you want to. It's not just something that "other people" do. You need to believe that, as I believe you've begun to already, so write that profile and get it posted. Find some new interests that your health permits you to pursue, because you'll meet new people that way, too. Your "past" is always going to be a part of you, but it doesn't have to stand in the way of your future.

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website — you can visit BG's blog to discuss this letter! A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your own dating questions for Ask Lynn via Your question may be answered in a future column.
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