It would be easiest to blame my near nonexistent romantic life on living in San Francisco, a place where it’s rumored to be impossible to date. I could say all the guys here are slackers or Peter Pans who rarely make a genuine effort, or that the only way either sex ever really makes a move is through the Internet. And I might blame my single status on my years of living in an urban setting where I’ve grown unapproachable and jaded, or on my age, my decaying reproductive organs, or how I no longer fit someone’s classic under-40-OkCupid criteria.

But dating has never been easy for me, and in high school and college my love life was just as lethargic. As a teenager, I would binge on wine coolers, make out with the cute boy from my English class, and on Mondays either ignore him or obsess over him quietly. As an undergrad, it was all the same only the details changed – a nineteenth-century lit class, a co-op party, and the option of hallucinogenics.


At 21, I gave up hope that my romantic life would ever morph into a John Hughes film, and I met my first boyfriend. After six years, he became my husband, and another eight years, my ex-husband. Initially all I thought I wanted was someone who played guitar, listened to the Replacements, and wore Sambas. And this pretty much describes my ex. He toured nine months of the year, liked bands on Touch and Go, and played soccer in college. But as I grew older, I realized our marriage had turned into a rock ’n’ roll cliché, including erstwhile drummers, band breakups, drugs, and hookups with groupies in Paris and London.

Ultimately, I couldn’t blame my ex since he did us both a favor – he behaved so badly that I didn’t have to feel guilty for wanting out (though inevitably I did) or take responsibility for my own mistakes. But I was still left shell-shocked. At 35, when most of my married friends were having kids and moving to the suburbs, I was single and struggling to make a living as a college instructor and freelance writer. I wondered if I’d completely wasted my 20s and a big chunk of my 30s.


But, as my therapist soon pointed out, a lot happened while I was ensconced in couple-dom. I went to grad school twice and traveled to five continents. I hit every state in the union, save Alaska, Maine, and Kansas, and every Waffle House in between. I learned how to make a soufflé, rewire an electrical outlet, and I became an excellent parallel parker. I also lost my dad and adopted a dog.

Yet divorce left me stunted, and very cautious about dating. While my premarriage instinct was to ambivalently fall into romance with a little help from a bottle of booze, my older single self isn’t a huge drinker and doesn’t want to date one. Thus, dating has become increasingly intentional. I’m forced to make decisions and follow my (somewhat unreliable) gut. Somehow I still manage to ignore guys I like, flirt with the ones I know I’ll never date, and rarely recognize the glimmer of potential until it’s well beyond my reach. I continue to make so many mistakes despite my years of experience.

But mistakes have led to some interesting adventures. I once dated a waiter-artist who was clearly a hoarder and possibly a Republican; a lifeguard-improvisational-comedian who rode a fixie and liked to call me Mrs. Robinson; a pop-culture enthusiast who referred to himself as a “dilettante”; and a guy I met at a friend’s wedding who turned out to be a pot farmer. There was a botanist who slept in a sleeping bag, a British surfer dad who lived in Santa Cruz off “investment income,” and a few industrial designers, graphic designers, architects, and urban planners. Of course, these are pithy summaries of no doubt complicated humans, but I’ve seen a constant, though trickling, stream of entertaining cohorts.


At this point, I’ve dated friends, friends of friends, and I’ve had blind dates. I’ve given my digits to men in bars and I’ve asked a few men out. I’ve been set up, and I’ve flaked. I’ve had brief crushes on guys I worked with, guys who didn’t work, guys who didn’t work out, and guys who were complete workaholics. So far nothing’s worked. But I learned a lot – about botany, hoarding, and fixies. I learned that the quickest way to lose a friend is to date one, and the quickest way to ruin a group of friends is to date within the circle. I’ve had some disappointments, dodged some bullets, and I’ve sabotaged myself again and again. I’ve also learned that sometimes I need to ignore everything I’ve learned – that though it can take months and sometimes years for me to heal, there’s always a new bus coming into the station.

I’ve heard other dating perspectives, too. I have a 33-year-old friend who’s lovely both inside and out, and pretty pissed about the dating options in SF. I look at her and I wonder, how can she be having a tough time? I also have other friends who – regardless of age ­– experience a lively stream of suitors. There are still others, both male and female, who’ve taken themselves out of the game – they’ve closed up shop and turned the lights off entirely. Sometimes I feel like I’m standing on the sidelines of the dating field of battle, surveying the carnage.


And then there’s my mom, who at 64, and after 13 years as a widow, started dating. She went on Craigslist, Yahoo Personals, and and met all kinds of men – younger men, older men, a hot Brit who rode a motorcycle, and a quirky DJ from Ohio. And then my Obama-loving mama met a thrice-married Libertarian sheep rancher who lived outside of Lodi, and they fell madly in love. They were married by two Buddhist priests at an Italian restaurant off the side of a rural highway; she wore a purple dress, silver shoes, and pink flowers in her hair. For the last two years she’s spent six months of the year voraciously traveling – Mexico, Croatia, Austria, and Italy. It’s like one day she woke up and swiftly fell down the rabbit hole.

This makes me think, we’re not helpless – no matter how old or young we are – when it comes to love. Odd, since I’ve always had this sinking feeling that after 40, life would end. I’d be too old to be the prodigal daughter, the ingénue, the under 30 up-and-coming author, or the mother and the wife. No one would flirt with me on the bus, kiss me at the stroke of midnight, or tell me they thought I was cute. But this isn’t all necessarily true. As I get older, my expectations continue to change. And despite sometimes feeling alone, I find there’s a calmness, an inevitability, and that I’m usually so distracted by doing all the things that I always wanted to do (but was afraid to try when I was younger) that I forget I should be looking for love. I forget I need to look up, pay attention, and actually make an effort to connect with other humans. But I admit now, I really do want to connect. And if I were to write a letter to my younger self, I’d tell her to keep the light on, even when it feels like the last bus has left the station.