‘I have never been on a date with a woman ever’

Chat at 1 p.m.

I'm a 39-year old male and currently single. I have never been on a date with a woman ever. I am now at a point in my life where I would like to venture out and get into the dating scene. I'm kind of a late-bloomer, so to speak. I come from a very loving and supportive family.

You may be asking why I haven't been on any dates with any women ever. Well, I can tell you that I had a very tumultuous experience during my high school years. Albeit, while I was in high school, I did have the prescience to realize that "if I buckle down and concentrate on my schoolwork, I can get out of here and start a new life with new friends, and people who like me for who I am and not for the kinda car that I drive or the type of clothes or sneakers that I wear." So I graduated from high school and eventually ended up attending a maritime academy, which was a terrific experience for me. I was around people who shared my interests. Eventually I worked aboard an oil tanker, but am now working out of that field.

To this day, I still have confidence issues. In high school, I was the loser who was afraid of the other kids. I had social anxiety. The football players were popular and got the girls. I never thought I was a good-looking guy at all and still think that I am an ugly human being today.

I currently seek monthly treatment for depression. I used to drink a lot, but as of today, I am sober. I decided to stop drinking because I felt it was holding me back in life.

As an aside, about a year ago, I asked out a woman at work. She seemed to hint at the fact that she was single. After I asked her out, she said that she wanted to keep the relationship professional, and I respected that. I never bothered her after that. Either someone will like you for who you are, or they won't. But it certainly hurt after I was rejected. And I was reeling from the rejection for a long time afterwards. Recently she decided to leave the company because she found another job. When I heard about this, my heart sank, but with time, I believe that my heart will heal. It’s a learning experience, I suppose. In hindsight, I feel that she didn't want to go out with me because A) She had a boyfriend B) She thought I was unattractive C) She has a kid already and didn't want me in her life or her kid's life. But, who knows, right? Out of all three possibilities, "B" is what scares me the most. Looking for any advice on how to move forward.

Please go easy on me. Yes, I was once a sailor, so some may think that I can take the ridiculing or derisive comments, but please go easy on me. Thank You.

– 39

I’m happy to hear you're seeking help. I do wonder whether your therapist-doctor people might recommend any other kind of treatment. If you find that you're hitting a wall and that things aren't getting better, please let them know. You said the word "monthly," and I have to wonder if this plan is giving you what you need.

I'm not sure what happened with the woman at work, but I assure you it's not a scary answer. It's possible that she told you the truth – that she just wanted to remain professional, maybe because she doesn't entertain work romance. If the worst-case scenario is that she didn't find you attractive, that's also OK. Think about how many people you see in a day and how many of them you don't find attractive. It doesn't mean you think those people are revolting or undateable; it just means you don't want to be the person who courts them and makes out with them. It’s totally normal to ask someone out and get rejected. Rejection is a huge part of life.

I have to wonder whether you might have different experiences with acceptance and rejection if you tried a dating app. Those apps come with their own baggage (people can feel overlooked, like one of too many, too quickly judged, etc.), but they do show you people who are actually looking (no guesswork, like in the office), and you get a sense of how populated the world is with single people who are want to meet someone. It can be a reminder that you're not the only one. Perhaps with some professional guidance the experience could be constructive. Maybe it's something to consider with the people you go to for help.

You seem like someone who can fall in love with a hobby, which is awesome. The more you're out in the world doing things you love, the better you might feel about yourself – and the more you'll get to talk to people who get you. That’s another thing to talk about with family. What can you do in the world that will make you feel engaged and part of something you like? Make a list. Then give some of those things a try.

– Meredith

Readers? Empathetic pep talk?