Moving Forward from Past Patterns

Leora Hoffman Associates - exclusive matchmaking for baby boomers in the Baltimore / DC Metro area

Couple having dinnerHenry and Jeanette, both in their 60’s, were introduced four months ago and got off to a great start.

Jeanette, widowed for three years, had been happily married for 27 years. Her late husband was a physician who handled all the finances in the relationship, while she raised their family and volunteered in the community.

Henry, an attorney in his late 60’s, was divorced for the past eight years. He had dated dozens of women, coming close to a committed relationship, but ultimately was left disappointed and disillusioned with love.

Their attraction for each other was immediate and palpable. Henry was warm, bright and funny. For the first time since Jeanette was widowed, she felt excited about her potential future with a new partner.

They began making plans to travel together for the first time. They discussed their relationship with their grown children, who were thrilled for them.

It all felt fabulous, until Jeannette called me to share her dilemma: As they were planning their trip, the issue of money came up.

She expressed to me that during their initial months of dating, Henry would always ask her to split the check whenever they went out, which bothered her.

She complied, but always felt uncomfortable taking out her wallet in a restaurant, something she had never done in her entire marriage. She told me that she believed in the concept of sharing, but preferred to contribute in her own way, such as cooking dinners for him, which she had done, or buying tickets to various events. She simply didn’t want to be handling a check at dinner, something she preferred Henry to take care of, consistent with her traditional values and experience.

I discussed Jeanette’s concerns with Henry and suggested that he should consider modifying his style, so as to make Jeanette feel more comfortable and secure.

He bristled at this suggestion, stating that he was tired of “always being the cash cow” with women and felt strongly that things should be divided equally. When I explained that equality could be achieved in different ways, he refused to consider how shifting his behavior could help support their new relationship. He stated that he wanted things to be “50-50”, or “not at all”.

Sadly, it was this difference that undid a promising relationship.

Despite their mutual chemistry, Jeanette could not accept Henry’s “dutch treat” ideal. Henry, for his part, saw himself as completely fair, while protecting himself from his fear of being exploited.

My offer to refer them to a couples’ counselor was rebuffed They never took that trip, and they ended up going their separate ways.


It doesn’t have to be that way.

Dating at this stage is filled with subtle negotiations. Henry and Jeanette tried to get through a difficult issue without the help of a counselor or outside advice, and their relationship broke down.

Had they been open to working with a professional, they might have salvaged a rare and special opportunity to have found love again.

In my many years in business, I have utilized many talented couples’ therapists, who have successfully helped clients clear such hurdles to eventually marry.

Do you think the issues between Henry and Jeanette were deal-breakers? Your thoughts are most welcome.

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