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When "A Tailor Near Me" Touches More Than the Hem of His Client's Clothes

December 23, 2025

By Dr. Bill Woodson

The ability of men to keep even longstanding friendships at a superficial level is legendary -- which makes it quite the occasion when two men make a surprisingly deep connection in the course of a routine purchase.

When being fitted for a custom suit, a certain level of physical intimacy and invasion of personal space is part of the process. But how unusual is it for an encounter to lead to such a depth of emotional intimacy?

We soon discover that Alfredo's talents as a confidant and his attributes as a man and a husband - and even as a book critic - are far richer than his tradecraft as a tailor might lead us to believe. What one might assume would be a simple, transactional relationship with Sam leads to a deeply personal reveal, not only of Sam but Alfredo as well. And it was a connection that Sam clearly appreciated, evidenced by his sharing his conversations with his wife Janet, and the subsequent, oft-repeated, almost desperate offers to host Alfredo and his wife Couma for dinner.

As remarkable and noteworthy as Alfredo’s display of exceptional empathy and listening skills, was his resistance to being vulnerable in return. While he did display a significant amount of vulnerability in sharing the challenge of his beloved Couma’s decline, he resisted Sam’s invitation to transition their relationship from purely business, to a social one that might include the two couples. It made for a striking contrast-- between intimacy and aloofness. Given the significant level of need for social support that would be common to anyone in the process of losing a spouse to Alzheimer’s, I found myself rooting for Sam, that his offer of a deeper social relationship with Alfredo might be accepted. In fact, this unfulfilled desire is part of what gives this play its power.

I’m someone who has always savored the mixing of disparate flavors. While I might now mix my rum raisin ice cream with raspberry chocolate chip, I’m the same person, in my 60’s, who relished mixing chocolate ice cream with vanilla when I was 10. And that same preference for contrasting yet complementary flavors deepened my appreciation for the elements that made these “two old men” different, even as we also saw what they shared in common. How they clearly held a deep appreciation for their respective wives, even as they held them differently—Sam enjoying the “all American pastime” of telling jokes about his wife--something Alfredo has no taste for.

The richness and clarity of Alfredo’s assessment of the complex and layered relationship between Sam and his lifelong friend Robert was an additional aspect of this performance that I savored deeply. Just as remarkable, perhaps even more so, were the through-lines and connections that Alfredo skillfully parsed, not only in how Sam regarded his father, but how Sam’s relationship with his father influenced Sam’s relationship with his friend Robert. How Sam’s relationship with his father, as well as his mother, shaped, and were reflected in Sam’s relationship with his wife Janet.

From Sam’s stories, how Alfredo saw in Janet motivations that Sam had previously been oblivious to (“She was concerned for your soul (Sam).”) The way that, from Sam’s reflections, Alfredo teased out Sam’s relationship to the qualities of financial security, and artistic expression. When Sam reflects on his relationship with his son Adam, admiring Adam’s brilliance while acknowledging, with perhaps a bit of guarded pride, that Adam is motivated by money—a quality Sam doesn’t share, well, while Alfredo doesn’t comment, we can practically see the wheels turning in his mind.

There is a special power to being so fully “seen” by someone through a connection that most of us would expect to be purely transactional. How many of us would lean into such an opportunity, as Sam did? And who among us would resist, as does Alfredo?

Dr. Bill Woodson is a management consultant, a DEI practitioner, and the founder of Conversations Across The Aisle (CATA) a local organization created to promote community healing by creating space for respectful dialog among people with differing beliefs. Bill claims both Sarasota and Washington D.C. as hometowns, having grown up in the Nation’s Capitol, but born at Sarasota Memorial Hospital. A frequent visitor to Sarasota from childhood, and a full-time resident since 2019, Bill moved to the Suncoast from Minnesota’s Twin Cities, where he led an MBA program at the University of St. Thomas, and earned a PhD in Organizational Leadership from the University of Minnesota.
Those interested in learning more about CATA, or receiving an invitation to a future CATA dinner/workshop, should write to info@cataprojects.org. Reference FST in your correspondence, and indicate whether you “lean Blue,” “lean Red,” or “lean Independent.”