Getting over a quick rejection

I forgot to tell you that I had a doctor's appointment and couldn't chat yesterday. Sorry.

I am a faithful reader of your column and I hope you can steer me in the right direction.

I am in my late 40s, and I went through a divorce about two years ago. The ink was no sooner dry on the divorce agreement when I was laid off. I do my best to keep my chin up and be optimistic, but after almost two years of single fatherhood and unemployment, I have only a part time job and one date to show for it.

I recently met a woman at work. She is in the final stages of her divorce. We talked a couple of times and we connected. I asked her out for coffee and we talked more. I have enjoyed talking with her, and I have felt engaged and challenged like I have never felt before. She is not looking for a serious relationship right now, but would like to have one at some point in the future.

I asked this woman out for coffee again, and I got a note back saying that she did not feel a deeper connection. She went on to say that since we work in the same place, she did not want a relationship with me outside of work (even though because of our schedules, we have almost no interaction at work). She added that there were changes she wanted to make in herself and her life in order to find the kind of relationship she wanted.

I felt confused, disappointed, and hurt. I felt like we did connect, at least enough for me to want to see her again. I can only guess, but I think she was uncomfortable with the fact we both work in the same place. I also think she was uncomfortable with our age difference (she is about 15 years younger). Beyond that, I wonder if I did or said something wrong (like possibly mentioning my children or my ex-wife).

So I am left to wonder what I need to do in order to find someone else. I have a fear of not having someone special in my life and winding up alone. Through the whole process of my divorce and losing my full time job, I have just felt alone. I do know that people (mostly at my church) care and will listen, but I still feel alone. I guess I could use some insight and another point of view.

– Trying to Be Optimistic in Metrowest

There are so many reasons why this woman wasn't the woman, TTBOIM. I mean, there's the age difference, her divorce (would you have been ready to date two years ago?), the workplace stuff, and your shared insecurities about the future. As much as water seeks its own level, she's probably looking for someone who can make her feel confident about her new, independent life. You can't be that person for her right now.

You need to stop focusing so much on what you don't have and start making a list of what you want. You know you want a full-time job, so that remains a priority. As for love, what are you looking for? Do you want someone with kids? Do you want someone your age? Who do you think would make a good partner? Honestly, that's what you should be talking about with friends at church. Your friends are supposed to listen to your rants about being lonely, but you can't limit the interaction to just that. It's more productive to ask these people to help you create the life you want for yourself.

As for what you did wrong on your date, well, probably nothing. Again, there were other negative forces at work with this woman. That said, you should keep long rants about sadness and exes to a minimum when you meet someone new. And make sure that you ask a lot of questions and smile. Happiness is attractive. I know that things seem bleak right now, but they're not. You're hunting for a new and exciting job, you're single and free to meet people, and you're a self-aware man who isn't going to push the right person away. If you believe all of that, someone else will too.

Readers? Was he on the right track with this woman at work? Advice about dating while under-employed? Can you give this letter writer a boost? What's happening here? Should he be trying to date at all? Is he asking too much of two years? Help.

– Meredith