#14) Dating Younger Woman

Does the age gap really matter?

Here I was in 2007, newly single for the first time since I was 23 years-old. It felt like riding a bicycle with training wheels, having to learn how to date all over again, with the added complication of navigating dating women! There are so many lessons I’ve learned since then, through living and dating. I want to tell my 41 year-old self all that I know now, and how to avoid the misunderstandings, hurt, heartache and even at times, the danger, but I am also wise enough to know that she wouldn’t listen. I had to live through my experiences, my misadventures. I had to discover what did and did not work, and begin my journey of self-exploration, a necessary ingredient for dating women.

After my first grown-up relationship with Jenny, who was older and constantly trying to sublimate me as a lesbian newbie, my next relationship was a total course correction. I often did that in dating: I would ping back and forth to extremes. Kristy was 29 years-old, lived in a not-yet gentrified part of Brooklyn, worked in photography, and was quirky and whip-smart. We met online, where her profile indicated she was seeking older women. In setting up our first date, she canceled existing plans—something I hadn’t asked her to do, but was a harbinger of our coming unbalance—and worked around my schedule of when I could find a babysitter and escape to the city. Our date was last minute, so rather than pick a restaurant, she suggested we meet on a street corner on the Lower East Side near where I parked my car, and find a place together. This was before LES was in vogue—it was more hipster, and I was excited to venture in and try something new!

I emerged from the parking garage into the early fall, still warm, evening air, and there she was:  Kristy had long blond hair, gorgeous blue eyes, a couple of inches shorter than me, and a really cool look and vibe. Upon seeing me, she stood and smiled, with a sort of shit eating grin like she had just been caught in mischief. I was in jeans and heels, with a fashionable short-sleeve top. She was in jeans, with Chuck Taylors and a tight t-shirt that showed off her curves. There was instant chemistry. I walked over to her, and in what seemed like instinct, we kissed on the lips, then walked hand-in-hand to pick out a restaurant.

Over dinner at a nondescript, half-empty restaurant, I learned that Kristy had dated men and women in college, but had only one serious-ish relationship, with a man. She was engaging and had an eclectic knowledge base: I had mentioned my involvement in Hillary’s campaign in an email, so she brought me campaign buttons from Truman and Mondale/Ferraro from her collection. Pretty cool stuff! As she spoke, her eyes intermittently darted back and forth, as if nervous, while in between she coyly beamed at me. I wondered, is this the age difference? She seemed deferential, which felt so dramatically different than Jenny, and was new ground for me in dating. After dinner, I drove her home, and she invited me in. The hour was getting late, and I told her I needed to get home to the babysitter, but after we started to kiss, we lost track of time, and soon our tops were coming off and we were feeling each other’s bodies. I noticed the clock, and told her I needed to leave. Before I left, we planned to get together in Manhattan during the week.

It’s funny, because when I dated Kristy, our 12 year age gap seemed enormous to me. I went into our first date pretty sure the gap made getting into a relationship a non-starter, but wanting to meet her because she was beautiful and compelling. Nowadays, dating someone with that age gap seems like nothing! I suppose it’s all relative: the older you get, the smaller the gap feels in proportion to your life. I have dated women twenty (or more) years my junior, and that can be challenging, because not only did you grow up in different eras with their own music and popular culture and all the rest, but there are also considerations of wanting to start a family and have children. For my gay male friends, dating much younger men is a sign of prestige and virility, as it is for men in heterosexual relationships, but that doesn’t really translate in the lesbian community.

When I think back, and try to recollect why the gap mattered to me so much back then, part of it was my own insecurity that a younger woman would put me on a pedestal, then later take me down, outgrow the relationship, and want to be with someone closer to her age. I also wondered what would attract someone to older women, although I was noticing many couples who successfully navigated their age gaps just fine. In retrospect, I was just starting to date and get my bearings. What I did eventually learn from years of dating was that the idea of mutuality and being on even ground was really important to me. I also learned in that pursuit, age was not always a determining factor.

Kristy messaged me the next day, saying Margaret Cho was in Manhattan for her tour, and asking if she should get tickets. I liked Kristy and had fun on our first date, but was concerned that she was getting really serious, really fast. I could feel myself pulling back, and putting on the emotional brakes. Could I really pull off having a relationship with a younger woman? The whole dating scene was still new to me. I wanted things to slow down, but didn’t want to hurt her feelings and just end it there. I understand now that there were other options of course, like putting things in a slower gear, but I didn’t yet have the emotional intelligence to open a conversation to make this happen—nor did she. Margaret was hilarious, and it was almost impossible not to be laughing and having a fun time, but each time I glanced over at Kristy, she was smiling and staring at me with adoring puppy eyes, and it made me feel uneasy. By the end, Kristy could sense my discomfort. When the show ended, we awkwardly hugged, and I pecked her on the check and said goodnight.

She emailed the next day, and it was so easy for me to stay drawn in. I liked her, wasn’t ready to give up on the possibility of an us, and I wanted to have a girlfriend. Part of me was afraid to be alone—then completely new territory. But our uneven paradigm continued, and the more effusive and adoring she became, the more I stepped back into my shell. Our third date, all within a little more than a week, was then just super awkward. I said yes because I didn’t want to hurt or disappoint her, but then felt uncomfortable and regretted that we didn't let some time pass before our third date. She seemed forlorn and unsure of what to do next. I drove her home after, and we kissed goodnight.

A week later, a package arrived from Kristy, containing an exquisite photograph titled “Heart of Glass,” along with a lovely note. She blamed herself for sabotaging things—a charge that was totally unfair and untrue. She told me I was amazing, sincere and compassionate, and lamented, in her elegantly written prose, that with me, every wonder and wish she had ever dreamed was right in front of her. The me of fifteen years ago was too emotionally unevolved to truly process this love letter in a constructive way. It gave me a flight response. I wanted to have someone in my life, and tried to think about how to deliver that message in a way that might give us a path forward. Or did I really want to pursue something with a much younger woman? I was unsure. We both took some time to let things breathe.

She came up to Westchester weeks later. To avoid the awkwardness of our last date, we opted for some privacy, staying home and ordering dinner in. Absence makes the heart fonder, and things eased. We chatted and laughed over sushi and hot sake, then I lit a fire in the fireplace, and we kissed and enjoyed each other’s bodies. Later, we headed upstairs, made love and spent the night in each other’s arms. When the sunlight came in, we woke up to each other with a certain, mutual understanding that whatever we had together, while lovely, was also over for now. I made Kristy a coffee for the road, we embraced, and said goodbye.

We remained friends. One thing Jenny the career lesbian and I had disagreed on was whether after an intense relationship, you could maintain a pure friendship. I had only meaningfully dated in the heterosexual world, so that was my reference point. My experience was if there was a real spark, it never totally fades. Years later, that did turn out to be my pattern with Jenny as you’ve read: we got back together, and ended up in bed. Kristy and I got together months later, ostensibly as friends, for an afternoon hike with my dogs, and sure enough, ended up in bed too. But after that, we did manage the friendship thing, and navigated it really, really well.

For years, Kristy and I stayed connected. When my kids and I decided to do a “12 Months of Arleen” calendar as our holiday gifts, Kristy helped with the photo edits. When I started The New Agenda and needed a professional looking photo for our website, I drove in and visited Kristy at work. When my daughter started playing high school sports and I wanted to figure out how to take high quality photos, Kristy drove up and we went for coffee. I came into the city for dinner or coffee when she needed career advice, or help negotiating salary or her next promotion. We caught up over beers and charcuterie at the High Line when it first opened. We stayed in each other’s lives, even as we both dated other people.

Five years later, I had one of those life changing events: someone I had known professionally and deeply respected died suddenly.