Willing. The Philadelphia Story: Cynthia and Phil by Lisa Ellex

Willing. The Philadelphia Story: Cynthia and Phil by Lisa Ellex

. 3 min read

Willing is our ongoing series about dating at this stage. It’s so complicated. We’ve got emotional scar tissue from umpteen years of living and loving and loss. We’ve got nerves. We’ve got the practical obstacles of baked-in structures and demands, familial and geographic. Too often, we just can’t break through. But then, sometimes we do.


Cynthia met “Phil” online. A handsome and successful widower, Phil had lost his wife a year earlier. He moved from Minneapolis after raising his kids there and was now a top CEO in Philadelphia.

Phil and Cynthia enjoyed a glorious year of dating; she had grown up in Philadelphia, was from a prominent family and a member of various golf and tennis clubs, and was fully integrated in an affluent social community. She introduced him to the city and her close-knit world there; he appreciated and enjoyed her and her friends and toward the end of their first year together, Phil made it clear that he wanted to move from his rental into a home Cynthia would be happy to live in.  With the help of her realtor friends, Cynthia found Phil a great place to purchase and offered to coordinate his renovation since she had more flexibility in her job than he did. Phil agreed. He told Cynthia that he felt their relationship was life-changing, and he would love it if they talked about moving in when the renovation was done. Thinking she had found the man, Cynthia was ecstatic.

Although Phil clearly expressed to Cynthia how much he loved this new life with her, they somehow never shared any vacation time. As a new CEO he had few days off and that luxury was reserved for taking trips with his two twenty-something daughters.  From Paris to the Bahamas to long weekends at upscale New York City hotels, no destination was too big of a splurge. Afterall, for Phil, money was no object; it was time that he lacked.  Since the passing of his wife, Phil had coveted his newly reformulated little family and considered his time with the girls as precious. So precious that Phil never took calls from them in Cynthia’s presence. Unbeknownst to Cynthia, Phil’s daughters never knew he was dating!

One day Phil announced he had some happy news to share: his eldest daughter was engaged and he would soon be off to Minneapolis to spend some celebratory time with her. Cynthia did not get invited to the daddy-daughter weekend.

Phil returned home with yet more news to share.  When he told the engaged daughter about his relationship with Cynthia, his daughter carried on about how she wasn’t ready for him to start dating (even though her mother had died (at that point) two years earlier). In her and her sister’s opinion, it was too soon.  They saw his action as a betrayal of their mother, and cautioned him that “this woman is taking advantage of your vulnerable state.”  And then Bridezilla gave her father an ultimatum:  “If you are still involved with her you cannot come to my wedding.”

Cynthia wondered just why his daughters would deprive Phil of such happiness, especially now that the engaged daughter had found her own.  She wondered, too, if Phil would allow himself to be manipulated in this way, especially after revealing to Cynthia that he considered their relationship to be so “life-changing” that they were planning a life together.

By his daughter’s edict, Phil had to end it with Cynthia in order to attend his daughter’s wedding. You can guess the rest.  Cynthia felt convinced that Phil’s daughters would rather cut him off than share his attention – and his wealth – with another woman. And that marvelously renovated apartment? Cynthia reveled in knowing it would never be large enough to fit Phil and any other woman– as long as Phil allowed his daughters’ demands to take up space.

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