A 40-year-old … something

Hi Meredith,

Like many of your readers nearing a certain age, I am now in the position of realizing I'm tired of being lonely and want to find a significant other. What may make me different from many others is a rather basic (yet vexing) problem: I've never been on a date, had a girlfriend or even women friends. Ever. Not in middle school, high school, college, and especially now that I'm an adult. I didn't even go to the prom. Oh, I've always gotten along with women as a student and on a professional level, but never anything deeper. There are many reasons and I have had other priorities over the years -- family (overcautious parents, dating never encouraged), personal issues (hard-wired introvert, very shyness, some social anxiety, etc.), economic (I have had to move several times for work and school and the impact of the Great Recession has taken a toll), and even academic/work (I've often had to buckle down at the expense of a social life).

What it all adds up to is a complete stalemate. In the past I was too timid, but now that I am older and a little more confident about what I want, I realize what I have missed and I'm tired of being lonely. In many ways, I am still the teenager who was attracted to girls but never had the mojo to move forward, burying my feelings so deep for so long that it hurts even to think about it. As I have considered my options and am trying to reach out (including coming up with a sensible online profile), I have come to the stark realization that I am totally clueless. I have rediscovered old hobbies and am also in therapy for the shyness, anxiety, etc. which are key factors in my situation. But I have no experience whatsoever with significant personal relationships. Therefore, I have nothing to work from or to fall back on, leading to a near total lack of confidence and low self-esteem. Don't get me wrong; in spite of everything I have said and how I must sound here, I know I am capable of love and of being that special someone to a special woman. And I want to be able to show that I can. I never had the chance, and would like know how and where to begin to help overcome all of these obstacles. Whatever help you could give is welcome. Thanks.

– 40 Year Old Something, Newton

First of all, everyone is clueless when it comes to online dating. You never know what words and pictures are going to attract the right mate. If I were you, I'd spend some time reading other profiles on these sites (men and women) to see how it's done. Then write up something that's 100 percent you. If/when you reach out to women who look nice, continue that honesty. You can absolutely say, "Hey, I'm new to this, but I like your profile." Ask them questions about their interests. Remember that if they're on the site, they're looking, too. I do think that online dating is a great way to jump into the game.

My big piece of advice, though, is to focus on friends. As we learned from the movie about another 40-year-old something, friends are the key to enjoying life and finding confidence. My assumption, based on your letter, is that you have some male friends. Do they have female friends? Do they have romantic partners? Can you hang out in a larger group?

They key to all of this is learning how to ask. If you want to hang out with someone after work, you have to be able to invite them. If you want to learn more about a woman online, you have to be bold enough to send a message. Your therapist should be able to help you learn how to make requests without panicking.

Please know that most people want to be contacted and asked out, even if they say no. Women are not robots. They fear rejection. They hope to find someone who understands them. And even though you're inexperienced, you're smart and self-aware. That goes a long way. Don't underestimate yourself.
Readers? Should he be dating online? How can he expand his circle? Thoughts about how he can bring some women into his life? Help.

– Meredith