Tom Blake, Columnist
On Life and Love After 50 eNewsletter
May 8 2026
As a senior dating columnist for 32 years, I’ve often been told by both men and women that meeting a potential mate is difficult, especially as we get older.
Four months ago, a male reader I’ve known for 20 years, relocated to Laguna Woods Village, an Orange County 55+, age-restricted community. For privacy matters, I will refer to him as Gordon, not his true name. He’s single and 73.
A month after Gordon had moved, he emailed me, “Well things are looking better dating wise for me in my new 55+ community, compared to when I was using online dating sites. I’ve even heard that online dating sites are becoming less popular among seniors.
“There are more than 250 social clubs in our Laguna Woods Village. I have met four women here. They all belong to clubs. I met two of the women on an Astronomy club daytrip to JPL in Pasadena. I did not realize that there were so many women in the club. Then I thought, ‘Hey they must be thinking if they want to meet a man, they must participate in clubs that feature activities men enjoy.’
“On the return bus trip from Pasadena, a woman sat next to me. She talked the whole way back. When we got close to returning, she started to scroll on her phone. She said she was getting rid of spam. What dawned on me after she got off the bus was, she was trying to tell me to give her my phone number. I didn’t, but oh well now I know where to find her!”
Gordon sent me a follow-up email last week. He wrote, “The possible dates I hoped to go out with did not happen for these reasons.
- One told me she is not looking for a relationship. She mentioned that we could just go out for lunch or dinner.
- Another woman said it was too soon to date after her significant other passed away. However, she also said we could go out for lunch or dinner.”
- There is an attractive woman who lives near me. One day that woman, and another woman and I were talking outside our homes. She mentioned that she had been married since she was in her twenties and that if her husband died, she would not be interested in another relationship.
- Not meeting the woman who sat next to me on the bus was my fault. I should have asked for her phone number and name. Silly me.
“So, my next possible idea that has been suggested to me is to go to one of the pools and spas here or to Clubhouse social events. There are several Clubhouses here. Each of them has spa. One is near me.
“I am also going to try Speed dating again. I have been to two of them since I have been here. The price of them is not bad. I have not had very many matches but what the heck?”
Tom’s Comment
Of the four women Gordon had met, one said she isn’t looking for a relationship. But she is willing to have lunch or dinner. If that happens, a nice friendship might evolve.
Another woman said it was too soon to date after her husband died. But she also would be willing to meet for lunch or dinner. Same thing, a nice friendship might evolve.
Another woman is married. Who knows? Someday she might want a non-romantic friendship. We all need them.
Gordon is now aware that in his four months of living at his new community, he’s blown several opportunities to meet and socialize with nice women. He should have asked the woman who sat next to him on the one-hour bus ride for her phone number and given her his number, but he didn’t. A missed opportunity.
My significant other, Debbie Sirkin, a psychotherapist, said “Some of the best relationships begin as friendships. Bill should make friends with the women he’s meeting at his 55+ Community and not worry about meeting potential partners; instead, he should make multiple women friends where he lives. I give Bill credit. At least he’s trying to meet new people.”
Tom concludes, “If the cost of lunch or dinner is too pricey for Bill, then switch to a coffee meeting, or after a first encounter, see if she might be willing to pay half, or switch to a walk or hike together.
At least Gordon has tried speed dating a couple of times. It gets him out socially. I did it once and fell on my rear. I was lucky, no injuries. At 73, he’s got to be careful to plant himself firmly on the chairs. In speed dating, trying to sit too soon is dangerous. There are plenty of other options for him to meet women where he now lives.
Also, with a ratio of approximately 7.5 women to each man in the community, Gordon should realize he’s living in a paradise for senior single men to meet senior single women. He needs to be assertive, not aggressive. Make friends first.
On Life and Love after 50 