Adam and I moved to Portland, Maine, on December 26, 1996. I rented a U-Haul trailer; hooked it up to my dark green Ford Explorer; filled it with our clothes, books, beds, and pictures; and off we went. My sister Lynn came with us to help.
I left all the furniture with Len. I wanted a fresh start, a new home, new people, and new things. Portland, Maine, was a breath of fresh air compared to uptight, status-driven Connecticut. I had never liked living there. It was conservative and pretentious even if everyone read the New York Times and thought of themselves as liberal.
I left all the furniture with Len. I wanted a fresh start, a new home, new people, and new things. Portland, Maine, was a breath of fresh air compared to uptight, status-driven Connecticut. I had never liked living there. It was conservative and pretentious even if everyone read the New York Times and thought of themselves as liberal.
My kids reacted to varying degrees to their own Connecticut experiences. Joel, who was a rebellious rocker with hair nearly down to his waist, tattoos, and an earring, never seemed to care what anyone thought about him and had lots of friends. He fit in just fine in uptight New Canaan. Rachel was more mainstream in her approach: going to college and working at a muffin shop. She seemed at home there too. Adam was another story altogether.
When Len had his stroke, Adam was thirteen, creative, artistic, and searching for his identity like all teenagers. At school he flourished in photography using pinhole cameras and experimenting with Polaroid film images by freezing them and scratching the surface.
His art teacher told me he thought Adam was a cutting-edge artist. I looked at his photos and couldn’t understand them. He liked to stage his pictures and set up plastic figures like toy soldiers and nun dolls in vignettes that made no sense to me at all. Years later I saw this exact work done by other artists in SoHo and other galleries. He was ahead of his time.
One Christmas Adam took Polaroid photos of Len, myself, and our dog then cut out our faces and pasted them over other things he had photographed. I remember one picture was of a wood and brass award Len had received. Adam put my face on the front between the brass olive leaves and renamed it “The Expensive Len Schutzman Award.” He also superimposed my face over a painting I had of a Hopi woman. She was holding a clay pot like an offering. It looked surreal. One time he took a copy of The Catcher in the Rye, stabbed it with a knife and set it on fire in the backyard then took a picture of it. I never knew what he would come up with next.
When Len had his stroke, Adam was thirteen, creative, artistic, and searching for his identity like all teenagers. At school he flourished in photography using pinhole cameras and experimenting with Polaroid film images by freezing them and scratching the surface.
His art teacher told me he thought Adam was a cutting-edge artist. I looked at his photos and couldn’t understand them. He liked to stage his pictures and set up plastic figures like toy soldiers and nun dolls in vignettes that made no sense to me at all. Years later I saw this exact work done by other artists in SoHo and other galleries. He was ahead of his time.
One Christmas Adam took Polaroid photos of Len, myself, and our dog then cut out our faces and pasted them over other things he had photographed. I remember one picture was of a wood and brass award Len had received. Adam put my face on the front between the brass olive leaves and renamed it “The Expensive Len Schutzman Award.” He also superimposed my face over a painting I had of a Hopi woman. She was holding a clay pot like an offering. It looked surreal. One time he took a copy of The Catcher in the Rye, stabbed it with a knife and set it on fire in the backyard then took a picture of it. I never knew what he would come up with next.
About the time Len had his stroke, Adam became obsessed with the cult classic The Rocky Horror Picture Show. We had the record and the video of it. He used to dress up like Dr. Frank-N-Furter wearing black fishnet stockings under his shorts and a top hat. He even went to school like that. He was never reprimanded or asked to change. When Adam found out local theaters had midnight shows with audience participation, he went to the shows dressed up and I sometimes went with him. I was too busy dealing with Len and the overwhelmed feelings I was going through to really take time to understand what the fascination with Rocky Horror was for Adam, although it was fairly obvious he liked the gender-bending aspects of the show as well as its punk-rock style.
The Rocky Horror fishnets segued into way more elaborate getups that moved into cross-dressing. Adam went to secondhand stores and started buying skirts and women’s sweaters. He raided my closet once for a party he was going to and found a kimono that he dressed up in with high heels and red lipstick. Sometimes he wore makeup, and once he wore a blonde wig that looked like faux Marilyn Monroe hair. Cross-dressing these days is more acceptable and understood, but still not mainstream. Cross-dressing back in 1994, in patrician Darien, Connecticut, took guts because no one dared do it.
I remember dropping Adam off at high school in the morning wearing his fishnets, a skirt, a tee shirt, and pink plastic barrettes in his hair and praying he wouldn’t get beat up. The school allowed him to dress that way. His homeroom teacher called me and said how much other teachers respected Adam for expressing himself. “Wow,” I thought. “That’s weird.”
I was told Adam was courageous and that by cross-dressing he helped other students who feared expressing their gender preferences. I found out that the board of education in Darien refused to send students to gender issue conferences and Adam’s acts of courage highlighted the need for the board to change its policy.
I could care less about that. I just wanted to know my son was safe and not going to be the target of some awful bullying. At first I was pretty horrified seeing Adam dressed up. Shit, how much more could I take in the wake of everything else that had happened to us as a family! I eventually started thinking: what difference did clothes make? I loved my son. If he felt he needed to cross-dress as a form of gender exploration or rebellion against all the crazy things happening in our family, so be it. I just wanted him to be happy and safe.
Joel had his rebellions too at this time, pushing the edge with his tattoos, extreme long hair, and rejection of college. Adam’s explorations were just another form of pushing the envelope further. Things could be worse. No one was using drugs or alcohol or doing other risky behaviors that could endanger themselves.
Maybe it was rebellion against his father’s meanness and living in a myopic town, or maybe it was a healthy way to explore his gender issues, or both, but once we moved to Portland Adam never cross-dressed again. Though it wouldn’t have mattered if he did. Portland was a very gay-friendly city and people there could be as wild as they wanted to be. Once we moved there, the pressure to conform to the Connecticut way of life disappeared.
For me, living in Portland as a single woman was baptism by fire. I did not have any LGBT friends. In fact, I didn’t know anyone who was gay. I didn’t know how to be politically correct nor did I understand all the different mores of behavior. I had a lot to learn. Moving to Portland was a new frontier for me to explore. I bought a two-family house on the Eastern Promenade from very cool guy named Crandall Toothaker. His name reminded me of a Dickens’ character.
The Rocky Horror fishnets segued into way more elaborate getups that moved into cross-dressing. Adam went to secondhand stores and started buying skirts and women’s sweaters. He raided my closet once for a party he was going to and found a kimono that he dressed up in with high heels and red lipstick. Sometimes he wore makeup, and once he wore a blonde wig that looked like faux Marilyn Monroe hair. Cross-dressing these days is more acceptable and understood, but still not mainstream. Cross-dressing back in 1994, in patrician Darien, Connecticut, took guts because no one dared do it.
I remember dropping Adam off at high school in the morning wearing his fishnets, a skirt, a tee shirt, and pink plastic barrettes in his hair and praying he wouldn’t get beat up. The school allowed him to dress that way. His homeroom teacher called me and said how much other teachers respected Adam for expressing himself. “Wow,” I thought. “That’s weird.”
I was told Adam was courageous and that by cross-dressing he helped other students who feared expressing their gender preferences. I found out that the board of education in Darien refused to send students to gender issue conferences and Adam’s acts of courage highlighted the need for the board to change its policy.
I could care less about that. I just wanted to know my son was safe and not going to be the target of some awful bullying. At first I was pretty horrified seeing Adam dressed up. Shit, how much more could I take in the wake of everything else that had happened to us as a family! I eventually started thinking: what difference did clothes make? I loved my son. If he felt he needed to cross-dress as a form of gender exploration or rebellion against all the crazy things happening in our family, so be it. I just wanted him to be happy and safe.
Joel had his rebellions too at this time, pushing the edge with his tattoos, extreme long hair, and rejection of college. Adam’s explorations were just another form of pushing the envelope further. Things could be worse. No one was using drugs or alcohol or doing other risky behaviors that could endanger themselves.
Maybe it was rebellion against his father’s meanness and living in a myopic town, or maybe it was a healthy way to explore his gender issues, or both, but once we moved to Portland Adam never cross-dressed again. Though it wouldn’t have mattered if he did. Portland was a very gay-friendly city and people there could be as wild as they wanted to be. Once we moved there, the pressure to conform to the Connecticut way of life disappeared.
For me, living in Portland as a single woman was baptism by fire. I did not have any LGBT friends. In fact, I didn’t know anyone who was gay. I didn’t know how to be politically correct nor did I understand all the different mores of behavior. I had a lot to learn. Moving to Portland was a new frontier for me to explore. I bought a two-family house on the Eastern Promenade from very cool guy named Crandall Toothaker. His name reminded me of a Dickens’ character.
Crandall was a tall, handsome guy with a smile and laugh that lit up a room. He and I hit it off right away. He loved rehabbing houses, interior design, fine food, and having fun. We were both straightforward, honest people, and the energy between us was easy and comfortable like reconnecting with a long lost friend. We were both Geminis. Our birthdays were five days apart. We were each other’s twin.
Crandall took me under his wing when I arrived in Portland, and at least two or three times a week for months took me out to dinner, auctions, movies or we just hung out with each other.
He encouraged me to start buying furniture for my new home. He helped me pick out colors, showed me how to bid at auctions, and spent time with me drinking and laughing. I never felt so free, supported, or happy, which added to my confusion. I knew Crandall had a partner, Frank, but Frank wasn’t around much and never joined us for our adventures. Crandall and I had fun all the time. I fell in love with him. He supported me in ways no one had before. I was a straight girl having a gay-guy experience and didn’t know it. I misunderstood our relationship and thought I was actually turning Crandall straight!
I will never forget the conversation I had with him about a year after we met. I had been telling my girlfriends about him and asking them for their opinions. None of them had gay friends so they were no help at all.
One afternoon Crandall came over, and as we were drinking wine and chatting on the back porch I worked up my courage and said, “Crandall, are you in love with me? Because I am in love with you.”
He started to laugh, turned red, and almost spit out his wine. “Missy,” he said, “I am gay but I love you like a sister,” and then gave me a big bear hug. I was embarrassed to have misunderstood this relationship for so long, but I also thought it was very funny that I was so naive.
I had spent a year thinking: “Is he or isn’t he? Now I knew. I think it caused a little friction between us. I remember he spent less time with me after that and his distancing felt hurtful to me. Then we started bickering with each other like siblings, but we always made up. All Crandall would have to do was smile at me and call me one of his nicknames, like Miss Muffit or Muffy, and I would melt.
We are still friends today and know each other’s secrets and laugh about these times. Both Crandall and Frank are beautiful people inside and out, kind, and fun to be around. They have seen me through thick and thin. I consider them to be one of the many blessings in my life.
Crandall advised me to start dating. He said I needed to kiss as many frogs as I could in order to find my prince. Len and I were separated but not divorced yet. Not being totally free put a damper on things, but I took Crandall’s advice to heart and decided to work hard at dating.
However, I dragged my feet for a long time before I start.ed to date. I had not been with another guy since I was seventeen. I wasn’t comfortable with men and couldn’t fathom how to talk to them, let alone go on blind dates from singles ads.
In 1998, once Adam moved out of our Portland house and I was on my own, I took the plunge. I started looking at ads in the local paper and found one guy that seemed safe. He said he was a Danny DeVito look-alike. I was attracted to his self-effacing humor. He sounded okay to me. I was very insecure about my own appearance and thought this guy was upfront about his imperfections and willing to be humorous about them, so why not give it a try.
We talked on the phone and wrote letters to each other. Yes, letters, imagine that! He regaled me with stories about his local theater experience and said he was a fabulous cook and wanted me to come to his place for dinner so we could get to know each other better. We never discussed age, but I knew from his voice he had to be at least in his fifties. I was forty-seven. He sounded confident, friendly, and sincere on the phone.
We met in August of 1998. My girlfriend Sue helped me choose some simple clothes and did my makeup. Off I went to his place in Brunswick, Maine, about forty minutes north of Portland.
I approached his house and was a little surprised to see that Bob lived year-round in a summer cottage in a makeshift community of other rundown cottages.
I knocked on his door and when he answered I saw a dwarf of a man. I was expecting short. I am only five foot two, but he was super-tiny, barely four foot ten. He had slightly pointed ears and was much older than he let on, maybe seventy or more.
“Oh boy,” I thought. I just wanted to turn around and run away, but I couldn’t think of a good excuse fast enough and I didn’t want to be rude. I felt sorry for the guy because he seemed to have gone to a lot of trouble for me. This is how I got sucked into the vortex of the evening.
As I walked into the cottage, I immediately stepped onto the enclosed summer porch that doubled as his living room. At close inspection, it was covered with mounds of animal fur. In fact wads of it rolled around like tumble weed across the aged linoleum floor and covered the black futon like a grey rug. Bob’s dog sat sphinxlike on the futon just staring at me.
Bob told me to sit down and ran back into the kitchen. He was a nervous wreck. With no clean place to sit on the porch, I followed him into the messy little kitchen and sat at the table, which seemed safe enough.
I tried to make small talk. I noticed that Bob had printed out the dinner menu on computer paper that had a lavender floral border and placed one on each dinner plate. He wrote the menu out like he was serving a gourmet dinner: first course, vichyssoise; second course, iceberg lettuce with tomatoes; third course, flank steak with Italian marinade; dessert, French chocolate chiffon pie. He did go to a lot of trouble.
I watched Bob as he nervously worked in the kitchen, which was a mess with dishes piled high in the sink, a dirty food processor on the counter, and pots and pans everywhere.
Whenever I asked a question or made small talk, Bob would stutter out an answer and make no eye contact with me. I thought, “This is a mistake! I should just leave now…
But I didn’t. I felt like a ball of lead, unable to move from the kitchen chair half out of curiosity, like watching a train wreck to see what’s going to happen next, and half out of fear and not knowing what to do. I wondered if the food would be sanitary enough to eat.
But I stayed and the evening continued. Bob finally sat down, read the menu like a waiter with a bellowing voice, and served the first course. It looked like paste. I refused to eat the white cold potato mush, making an excuse that I was allergic to potatoes. The salad course came and I picked at the mostly white lettuce leaves and pale red tomatoes splattered with Kraft Italian dressing. The meat came next; I took a bite and it was gristly. Okay, one more course to go and then I would leave! Bob got up and went to the freezer and took out his pièce de résistance, a frozen Banquet chocolate pie right out of the box. “Oh boy,” I thought, “can it get worse than this?
The evening was a bomb, but it was a funny story to tell.
After dessert I made an excuse and left quickly. Days later I got a letter from Bob telling me he had never expected me to be such a “looker.” He said meeting me had been nerve-racking and caused him to have diarrhea for the next three days! TMI! Poor guy. I did feel for him, but he had also misrepresented himself. He was frog number one.
The German ex-stock broker came next. He was wealthy and lived on the water in Falmouth, Maine. He owned several houses and an office building in Portland that he bragged about. He had a thick German accent and kept calling me “bootiful.”
I was a sucker for his European manners, his accent and fancy clothes, but he was also weird. He told me about the other women in his life and it sounded like he wanted more of a slave than a relationship. He wanted someone he could show off, but also someone to cook for him and keep secluded in one of his houses.
He owned a small boat and took me out to the islands in Casco Bay, a big attraction for me. He refused to get an AIDS test, which was the number one rule before intimacy back then. He did make me feel attractive and desirable, but it went nowhere fast. I spent one night with him at his house, but there was no sex. By accident, I left my best pink lace underwear there because I left in a hurry the next day. He sent them to me in an envelope along with a handful of crazy seashells with Santa faces painted on them as a parting gift. Go figure!
There were a few other dates where I was rejected straight out. One guy told me I was too fat for him. Another guy, who had some kind of skin disease that made his face mottled beige, white and pink, told me I was too old for him! Not only was he scary to look at, but he was also ten years older than I was!
Dating was a crapshoot, and I was not having any luck or fun. I kept busy by moving from my two-family home on the Eastern Prom to a smaller house closer to the water in Cape Elizabeth. I took a hiatus from dating. I had so much to share but no one to share it with.
I was forty-seven, lonely, sex-starved, and still not making any connections with men. My oldest son Joel thought I was gay since my hair was very short and I only wore baggy linen clothes to hide my weight. I never talked about dating with my kids, so they had no idea what was going on with me.
One of my problems was I didn’t know how to be seductively feminine. I never did know how to flirt or play games to make a guy interested in me.
Years before, when Len and I were separated, my friend Lee and I went out to dinner at a beautiful French restaurant. At dinner I thought the waiter looked cute and took it upon myself to tell him as I ordered that I was recently separated, thinking this was a clever way to send him a message! Lee just rolled her eyes at me. “What did I do wrong?” I said. I was clueless.
When the waiter came over again, Lee started to flirt with him. They hit it off and she ended up on a date with him! I was furious with her, but it made me very aware that I had no ability whatsoever to talk or flirt with men.
As it turned out, Portland was not an easy place for a straight single woman to find a partner. It was a great place to live if you were married or gay, but not single and straight.
I started to wonder if maybe I should think about being with a woman! What I wanted was the comfort of a partner: someone to share my life with, someone to laugh with and someone to love. Portland had made me a simpler woman, and I sensed life might be less complicated with a woman partner. I had one girlfriend who was also thinking the same way, or so I thought. She had been in and out of some bad relationships with men. She was ten years younger than me but we had similar interests and energy. She kept telling me how much she loved me.
We talked about art and music and went dancing at the local clubs. We kayaked together and enjoyed hiking, too. We cooked together, invited friends over, and entertained a lot.
I was so naïve. I thought we were a good match. I didn’t realize that she was a tease. She came on to me many times, but then she always backed off and acted like she wasn’t interested. I couldn’t figure her out. Maybe she was ultimately afraid of intimacy because I saw her do this behavior with others, too. I then got an insight: maybe she was the kind of woman who leads you on then dumps you I had heard men complain about. I realized it was a power game. It surprised me that a woman friend would be so calculating. Up until that point, we had had a very honest and clear relationship. No one had been back-stabbing or hurtful, but I guess when you add sex to the equation anything can happen.
The idea that being with a woman would be a natural progression from girlfriend to partner ended right there. I was back to square one, finding a man. It was 1999. It had been seven years since I had been intimate with anyone. All my efforts to end this dry spell had failed: it looked like I would be meeting a lot of frogs with no end in sight. The new millennium was just around the corner, though, and I was ready for a change. I had no idea that the change I was going to encounter would be more like an earthquake.
Crandall took me under his wing when I arrived in Portland, and at least two or three times a week for months took me out to dinner, auctions, movies or we just hung out with each other.
He encouraged me to start buying furniture for my new home. He helped me pick out colors, showed me how to bid at auctions, and spent time with me drinking and laughing. I never felt so free, supported, or happy, which added to my confusion. I knew Crandall had a partner, Frank, but Frank wasn’t around much and never joined us for our adventures. Crandall and I had fun all the time. I fell in love with him. He supported me in ways no one had before. I was a straight girl having a gay-guy experience and didn’t know it. I misunderstood our relationship and thought I was actually turning Crandall straight!
I will never forget the conversation I had with him about a year after we met. I had been telling my girlfriends about him and asking them for their opinions. None of them had gay friends so they were no help at all.
One afternoon Crandall came over, and as we were drinking wine and chatting on the back porch I worked up my courage and said, “Crandall, are you in love with me? Because I am in love with you.”
He started to laugh, turned red, and almost spit out his wine. “Missy,” he said, “I am gay but I love you like a sister,” and then gave me a big bear hug. I was embarrassed to have misunderstood this relationship for so long, but I also thought it was very funny that I was so naive.
I had spent a year thinking: “Is he or isn’t he? Now I knew. I think it caused a little friction between us. I remember he spent less time with me after that and his distancing felt hurtful to me. Then we started bickering with each other like siblings, but we always made up. All Crandall would have to do was smile at me and call me one of his nicknames, like Miss Muffit or Muffy, and I would melt.
We are still friends today and know each other’s secrets and laugh about these times. Both Crandall and Frank are beautiful people inside and out, kind, and fun to be around. They have seen me through thick and thin. I consider them to be one of the many blessings in my life.
Crandall advised me to start dating. He said I needed to kiss as many frogs as I could in order to find my prince. Len and I were separated but not divorced yet. Not being totally free put a damper on things, but I took Crandall’s advice to heart and decided to work hard at dating.
However, I dragged my feet for a long time before I start.ed to date. I had not been with another guy since I was seventeen. I wasn’t comfortable with men and couldn’t fathom how to talk to them, let alone go on blind dates from singles ads.
In 1998, once Adam moved out of our Portland house and I was on my own, I took the plunge. I started looking at ads in the local paper and found one guy that seemed safe. He said he was a Danny DeVito look-alike. I was attracted to his self-effacing humor. He sounded okay to me. I was very insecure about my own appearance and thought this guy was upfront about his imperfections and willing to be humorous about them, so why not give it a try.
We talked on the phone and wrote letters to each other. Yes, letters, imagine that! He regaled me with stories about his local theater experience and said he was a fabulous cook and wanted me to come to his place for dinner so we could get to know each other better. We never discussed age, but I knew from his voice he had to be at least in his fifties. I was forty-seven. He sounded confident, friendly, and sincere on the phone.
We met in August of 1998. My girlfriend Sue helped me choose some simple clothes and did my makeup. Off I went to his place in Brunswick, Maine, about forty minutes north of Portland.
I approached his house and was a little surprised to see that Bob lived year-round in a summer cottage in a makeshift community of other rundown cottages.
I knocked on his door and when he answered I saw a dwarf of a man. I was expecting short. I am only five foot two, but he was super-tiny, barely four foot ten. He had slightly pointed ears and was much older than he let on, maybe seventy or more.
“Oh boy,” I thought. I just wanted to turn around and run away, but I couldn’t think of a good excuse fast enough and I didn’t want to be rude. I felt sorry for the guy because he seemed to have gone to a lot of trouble for me. This is how I got sucked into the vortex of the evening.
As I walked into the cottage, I immediately stepped onto the enclosed summer porch that doubled as his living room. At close inspection, it was covered with mounds of animal fur. In fact wads of it rolled around like tumble weed across the aged linoleum floor and covered the black futon like a grey rug. Bob’s dog sat sphinxlike on the futon just staring at me.
Bob told me to sit down and ran back into the kitchen. He was a nervous wreck. With no clean place to sit on the porch, I followed him into the messy little kitchen and sat at the table, which seemed safe enough.
I tried to make small talk. I noticed that Bob had printed out the dinner menu on computer paper that had a lavender floral border and placed one on each dinner plate. He wrote the menu out like he was serving a gourmet dinner: first course, vichyssoise; second course, iceberg lettuce with tomatoes; third course, flank steak with Italian marinade; dessert, French chocolate chiffon pie. He did go to a lot of trouble.
I watched Bob as he nervously worked in the kitchen, which was a mess with dishes piled high in the sink, a dirty food processor on the counter, and pots and pans everywhere.
Whenever I asked a question or made small talk, Bob would stutter out an answer and make no eye contact with me. I thought, “This is a mistake! I should just leave now…
But I didn’t. I felt like a ball of lead, unable to move from the kitchen chair half out of curiosity, like watching a train wreck to see what’s going to happen next, and half out of fear and not knowing what to do. I wondered if the food would be sanitary enough to eat.
But I stayed and the evening continued. Bob finally sat down, read the menu like a waiter with a bellowing voice, and served the first course. It looked like paste. I refused to eat the white cold potato mush, making an excuse that I was allergic to potatoes. The salad course came and I picked at the mostly white lettuce leaves and pale red tomatoes splattered with Kraft Italian dressing. The meat came next; I took a bite and it was gristly. Okay, one more course to go and then I would leave! Bob got up and went to the freezer and took out his pièce de résistance, a frozen Banquet chocolate pie right out of the box. “Oh boy,” I thought, “can it get worse than this?
The evening was a bomb, but it was a funny story to tell.
After dessert I made an excuse and left quickly. Days later I got a letter from Bob telling me he had never expected me to be such a “looker.” He said meeting me had been nerve-racking and caused him to have diarrhea for the next three days! TMI! Poor guy. I did feel for him, but he had also misrepresented himself. He was frog number one.
The German ex-stock broker came next. He was wealthy and lived on the water in Falmouth, Maine. He owned several houses and an office building in Portland that he bragged about. He had a thick German accent and kept calling me “bootiful.”
I was a sucker for his European manners, his accent and fancy clothes, but he was also weird. He told me about the other women in his life and it sounded like he wanted more of a slave than a relationship. He wanted someone he could show off, but also someone to cook for him and keep secluded in one of his houses.
He owned a small boat and took me out to the islands in Casco Bay, a big attraction for me. He refused to get an AIDS test, which was the number one rule before intimacy back then. He did make me feel attractive and desirable, but it went nowhere fast. I spent one night with him at his house, but there was no sex. By accident, I left my best pink lace underwear there because I left in a hurry the next day. He sent them to me in an envelope along with a handful of crazy seashells with Santa faces painted on them as a parting gift. Go figure!
There were a few other dates where I was rejected straight out. One guy told me I was too fat for him. Another guy, who had some kind of skin disease that made his face mottled beige, white and pink, told me I was too old for him! Not only was he scary to look at, but he was also ten years older than I was!
Dating was a crapshoot, and I was not having any luck or fun. I kept busy by moving from my two-family home on the Eastern Prom to a smaller house closer to the water in Cape Elizabeth. I took a hiatus from dating. I had so much to share but no one to share it with.
I was forty-seven, lonely, sex-starved, and still not making any connections with men. My oldest son Joel thought I was gay since my hair was very short and I only wore baggy linen clothes to hide my weight. I never talked about dating with my kids, so they had no idea what was going on with me.
One of my problems was I didn’t know how to be seductively feminine. I never did know how to flirt or play games to make a guy interested in me.
Years before, when Len and I were separated, my friend Lee and I went out to dinner at a beautiful French restaurant. At dinner I thought the waiter looked cute and took it upon myself to tell him as I ordered that I was recently separated, thinking this was a clever way to send him a message! Lee just rolled her eyes at me. “What did I do wrong?” I said. I was clueless.
When the waiter came over again, Lee started to flirt with him. They hit it off and she ended up on a date with him! I was furious with her, but it made me very aware that I had no ability whatsoever to talk or flirt with men.
As it turned out, Portland was not an easy place for a straight single woman to find a partner. It was a great place to live if you were married or gay, but not single and straight.
I started to wonder if maybe I should think about being with a woman! What I wanted was the comfort of a partner: someone to share my life with, someone to laugh with and someone to love. Portland had made me a simpler woman, and I sensed life might be less complicated with a woman partner. I had one girlfriend who was also thinking the same way, or so I thought. She had been in and out of some bad relationships with men. She was ten years younger than me but we had similar interests and energy. She kept telling me how much she loved me.
We talked about art and music and went dancing at the local clubs. We kayaked together and enjoyed hiking, too. We cooked together, invited friends over, and entertained a lot.
I was so naïve. I thought we were a good match. I didn’t realize that she was a tease. She came on to me many times, but then she always backed off and acted like she wasn’t interested. I couldn’t figure her out. Maybe she was ultimately afraid of intimacy because I saw her do this behavior with others, too. I then got an insight: maybe she was the kind of woman who leads you on then dumps you I had heard men complain about. I realized it was a power game. It surprised me that a woman friend would be so calculating. Up until that point, we had had a very honest and clear relationship. No one had been back-stabbing or hurtful, but I guess when you add sex to the equation anything can happen.
The idea that being with a woman would be a natural progression from girlfriend to partner ended right there. I was back to square one, finding a man. It was 1999. It had been seven years since I had been intimate with anyone. All my efforts to end this dry spell had failed: it looked like I would be meeting a lot of frogs with no end in sight. The new millennium was just around the corner, though, and I was ready for a change. I had no idea that the change I was going to encounter would be more like an earthquake.