Homeless Friend didn’t start out as a homeless friend. Thanks to events that he actually could control, he bankrupted not only himself, but his 80-year-old mother as well. When I met HF, he presented an idea to work with me on a Roadside-related project that involved photo parodies of placemats and other related ephemera one might find in diners. Nothing ever became of that, but I became enamored of HF’s sense of humor, his professed appreciation for my efforts, and his then-girlfriend, a wonderful hostess who also had a beautiful house right across the river from mid-town Manhattan.
Over the next few years, the three of us would often think of ways to collaborate on some project for the magazine. The discussions never produced much, but few things ever came of the hundreds of similar discussions I had with dozens of other people. Despite that, we had a mutually beneficial relationship based on our kindred sensibilities for preservation, design, and humor.
When HF came to me with the news that he and his girlfriend had broken up and that she asked him to move out, it made me wonder why he’d let that happen. The girlfriend wanted to get married and HF wouldn’t commit. However, they not only had a personal relationship, but a professional one as well, and I wondered what HF would now do for a living. In truth, I had no idea how HF made any money in the first place, but he always dressed sharply and lived a lifestyle of — if not the idle rich — the comfortable Bohemian. I would not learn until much later that HF did indeed have a trust fund, but one better funded for a retirement nest-egg rather than one to maintain a jet-setting lifestyle.
In the post-girlfriend era, HF became some kind of entertainment consultant, but one that seemed to work for free. He often complained that clients failed to pay him for his services, despite the time and money he spent with them. Thanks to his bone-dry sense of humor, he led me to believe he made these remarks with tongue planted firmly in cheek. I often wondered if the guy didn’t live in some kind of fantasy world, wining and dining executives from the NFL, David Bowie’s managment company, and other top-shelf entertainment companies. In this realm, HF just didn’t have any leverage. How could he enforce any contracts?
After I moved down to the Philadelphia area, I actually saw more of him, because he had retreated to an apartment in southern New Jersey he never relinquished, and we had him as a frequent guest for dinner. During and after the meal, he and I spoke often about what we could do with Roadside and proposed to put me in touch with this guy or that company that might help relaunch Roadside. Over time, it got to the point where I found myself becoming annoyed with these discussions because they seemed utterly pointless. He just liked to hear the sound of his own voice.
Finally, I said to him, “Enough. Unless you have a meeting set up with someone serious, then can we please just drop this discussion?” Besides, at times, I couldn’t tell when he was joking or serious, and I also had doubts he could actually make anything happen. Ever.
Homeless Friend eventually began to sound off ever more urgently about his financial situation. “This time, it’s very serious.” Uh huh. Every time it seemed serious, and yet when he visited, he would bring over a bottle of Bordeaux or a bottle of good Scotch, plus French bread, brie, and other items he didn’t find at the local Acme supermarket. The guy had expensive tastes, which despite the imminent poverty, he didn’t want to let go.
Finally, it happened. A line was crossed, sort of. He asked me to pay a bill online, but he would immediately reimburse me with cash. Amex closed down his card, and his checking account ran dry. Now he began to talk about the specter of homelessness, not only for him, but for his mother who lived next door.
From that point on, it got no better. The eviction notice came. Talks with relatives to bail him and his mother out went nowhere. A court challenge failed. He and his mom had to go.
During this process, HF finally explained a great deal. Yes, he did have a trust fund in the six-figure range, but he depleted it on speculative business dealings. That and the effort to maintain the facade of an executive lifestyle finally caught up with him. He not only blew through his nest egg, but his mother’s as well. As a result, he had to help his mom declare chapter 7 bankruptcy so that she might qualify for Federal medicaid assistance and get into assisted living.
Yet, even as this was all happening, HF would come over for dinner — and now to stay overnight — and talk of how he could help Roadside. Now I looked at him and said, “Excuse me? How do I tell you this, [HF]? It’s GAME OVER. Let’s just stop talking about all this right now.”
He stayed over a few nights, and we were mostly happy to have him. I didn’t care much to think about him sleeping in his car, but I thought maybe finally he would answer the wake up call and get a job — any job — to get some income rolling in. Two months later, that still hadn’t happened. He emailed and asked if he might make use of our guest room, as another friend who recently took him in needed the bed for a visiting relative. We agreed, and then suggested he might stay through the weekend and house-sit while we traveled up to New England.
In the weeks we didn’t talk to him, his mother had become gravely ill, going in and out of hospitals, but finally landed in a less-than-optimal assisted living facility in Philadelphia. At least things seemed stabilized in that regard. However, while in New England, HF emailed me, telling me that something happened at the facility and that he had to take his mother out of there and let her sleep on our couch. If that development didn’t alarm me enough, a couple of hours later, he wrote again saying his mom had fallen down in our living room — but seemed fine.
With the prospect of liability for his mother’s injuries now looming over me and my family, HF had finally pushed it too far. I felt I finally had to say goodbye to the guy would would go out and buy not one Armani suit on sale, but five, despite his lack of need for even the one; the guy who asked us to store about a dozen pairs of fine Italian shoes — never worn — in our attic; and the guy who after three months out on the street still insisted on bringing a bottle of expensive wine before coming over for dinner.
I don’t decide to cast off a friend lightly, but nowhere in my definition of the term “friend” will you find an unconditional acceptance of liability. We friend those who bring value to our lives in some way, and while it sounds calculating, I think all of us maintain a kind of mental balance sheet that provides an ongoing assessment of our relationships. Make me happy, and I want you in my life. Waste my time, and I find other things to do. Cause harm to me or my family, and I want you gone.
I wish HF the best, and I sincerely hope he gets his act together and soon. He’s a few years older than me, but he possesses great intelligence and talent, and I have no doubt that he’ll find his way out of this and maybe learn a lesson or two. Until then, there’s nothing more I can or want to do. Like all of us, I have my own problems.