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On Life and Love After 50: The Bumpy Road of Senior Dating

by Dana Point Times
October 14, 2022 3:45AM
in DP LIVING, DP Living Headlines
On Life and Love after 50: Widow Puzzled by a Friend’s Warning

Tom Blake

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Tom Blake

By Tom Blake

Let’s say you’re 60 or older and single again. You might be divorced or in the process of getting a divorce. Or perhaps you’re a widow, or a widower.

You admit you are a bit lonely, so you’ve decided to put yourself out there in the dating world in hopes of meeting a compatible mate.

You are committed to getting off the couch and out of the house to focus on interacting with friends and meeting new friends. Perhaps you are considering online dating.

You don’t want marriage, just someone you’d enjoy being with. Someone who shares your values and interests. You’ve managed to have a few dates, but no one has clicked yet.

And then someone comes along who adds a little spark to your life. You think that perhaps a relationship could evolve. It’s hard, because you find yourself comparing that new person to your ex, and they don’t have the qualities that your former partner had.

You’ve had some interesting conversations with the person, which have revealed a small red flag or two.

Take, for example, Jane (not her true name), an Orange County resident who emailed, “Four months ago, I met Bill (also not his true name) online. He’s been separated for two years from his wife of 26 years.

“On our first date, the hours flew by. We had fun conversation and seemed to connect. Afterward, he emailed saying he had a great time, and our interests were similar.

“I wrote back expressing two concerns based on our discussion. One being that he is from Canada (his company transferred him to the OC) and his family lives 16 hours away. What would happen if he got homesick and wanted to move back there to live?

“And second, his marital status: separated two years. What is really going on there?

“He assured me that he’s here to stay, that his family is in full support of his being here, and his divorce is pending because he owes his attorney money and that was all that was needed to get the ball rolling.”

While Jane intended to proceed slowly with Bill, she rationalized that she, too, was once in the same position: separated, heart ready to move on, but with a legal system that can take a long time to finalize a divorce.

Jane added, “I have seen his divorce papers, so I know he’s working on the final stuff, and he was truthful with me. I gave him a chance, because I, too, had someone take a chance on me while I was waiting for my divorce to be final.

“We’ve had an awesome four months together. He helped me with remodeling my townhouse, and he met my family. We spent a weekend away exploring galleries and hiking. We enjoy our downtime after work and making dinner together—enjoying the domestic side of life.

“Then, suddenly, the rug was pulled out from under my feet. Now, he’s telling me that his head says one thing but his heart another, that there is a wall up. Apparently, he was hurt as a teenager by a relationship and again when he arrived in California. It’s taken six months to get over his latest heartbreak. He thinks if people must work at a relationship, it’s not the real thing.”

Jane rationalized again, stating: “He is bewildered and confused by his feelings, due in part to a lack of dating experience. This guy hasn’t ‘found’ himself yet.

“I must let time take care of things. I like him, but only he can find himself. He feels bad that he hurt me. His being in my life has been a positive thing; I experienced how wonderful it is to have someone really treat me like a woman, which I haven’t experienced in a very long time.”

I hear what Jane says, but Bill didn’t treat her like a woman for long. Her situation reminds me of the 2004 book He’s Just Not That Into You.

Seniors who choose to date again need to trust their instincts and keep their expectations in check.

Tom Blake is a retired Dana Point business owner and resident who has authored books on middle-aged dating. See his website at findingloveafter50.com. To comment: tompblake@gmail.com.

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Tags: CompanionshipDana PointDatingdivorceLoveOn Life and Love After 50Orange CountyRelationshipsSan ClementeSan Juan CapistranoSenior Dating
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