THE BLOG
02/11/2014 05:41 pm ET | Updated Apr 13, 2014

What I've Learned From Asking A Boyfriend About His Past Lovers

Chad Baker/Jason Reed/Ryan McVay via Getty Images

"Tell me about your girlfriends," I ask the man I've been seeing for the last few months, my bare leg sprawled over his, my fingers grazing the graying hair of his chest. He holds me closer and begins to talk.

My relationship with Jeff was young, but we weren't. At the time, I was in my late thirties, a single mom a year removed from the end of an eighteen-year relationship.

He's ten years older, tall and fit, with silver curly hair and Delft blue eyes.

I want to hear about Jeff's girlfriends not for the intimate details about those relationships (he's not the type who would ever kiss and tell, anyway) but because learning about his past makes me feel closer to him. Plus, I'm nosy -- although I like to think of it as "being curious."

Dating in midlife is quite different from the last time I dated, in college. Then, there was still a shiny newness to it; everyone I met had only recently shed the protective wrappers of childhood. We each had fewer years of relationship experience than fingers on one hand. My college boyfriend and I had had other lovers before we got together during our sophomore year. But those early forays into sexual relationships were far more sexual than relationship; with inept fumbling in assorted cars and dorm rooms, it was mutual lust rather than lasting love. Youth may be exuberant, but it often doesn't know what the hell it's doing.

Jeff had dated for far longer than I had. With decades of dating backstory, he was a bit like a book I'd been dying to read but one that started at chapter ten. I wanted to find out what happened in the previous chapters. It was, after all, the prologue to our relationship.

When my ex and I had met, we were essentially children. At nineteen, I was still a teenager. And like kids on a really great play date, we didn't want the fun to end. We quickly became close, spending all our time outside of our classes together. We slouched on the grass of the quad, grabbed (too many) post-study drinks at an off-campus bar and, a few hours after that, huddled in a diner's red vinyl booth, feeding each other greasy scrambled eggs and bacon. We skipped classes far too often, instead spending the day naked on his futon under the navy polyester-and-cotton blend comforter he'd brought from home, the one that made me itch and sweat in New Orleans's humidity. When we graduated, we didn't really discuss our future -- we both just assumed that we'd stay together. And we did, for almost two decades. Then it was over, a twisted Theory of Relativity, parts of our universe expanding and each of us moving away from the other seemingly faster than the speed of light. For a year, I focused all my energy on our young daughter and surrounded myself with friends. It was more than enough until one day it suddenly wasn't.

I was determined to meet someone -- or someones -- but, because of the large gap in my dating resume, I wasn't quite sure how. In college, everyone wanted to connect with someone, for a night or for far longer. Now the only men I met were married to my mom friends. I saw other men, lurking in my favorite cafe and at the local food co-op, so I knew they existed, but they seemed strange and exotic and as approachable as the Yeti. So how did a middle-aged single mom of a young child meet men?

I asked my ex-sister-in-law (with whom I'd remained close) when we got together at a cafe for drinks. She suggested I give online dating a try -- she'd met her husband that way. Sipping a glass of sauvignon blanc, she leaned closer on the edge of her chair and reminded me to practice safe sex. (I was actually going to have sex! ...if I met someone). She plonked her glass on the table and warned me that some men actually lie and say they're not married when they really are. I suddenly felt gullible and incredibly naive. The last time I dated, no one was married and cordless phones were the size of cereal boxes. Forewarned and forearmed (she'd given me a couple condoms), I joined a dating website, threw together a profile and uploaded a digital photo.

Jeff quickly responded, sending me a thoughtful letter, and I immediately wrote him back. It was like a game of tag by email. As soon as one of us received a note, the other would reciprocate. Neither of us wanted to be the first one to stop writing. Email led to phone calls that led to a real-life meeting that led -- eventually -- to me snuggled into him, asking about his ex-girlfriends.

Jeff had an entire life before we met which, to me, sounded terribly fascinating and glamorous. He was a writer in New York City, and he'd met and dated a slew of interesting, talented women: dancers and writers, actresses, social workers and businesswomen. I moved closer and asked about the other women, the earlier ones. What were they like? Why had the relationship ended?

"So what happened with Anna?" I asked. (Anna isn't her real name.)

"We were just at different places in our lives," Jeff said, slowly. "She'd married young and divorced right before we met. She wanted to see what was out there."

I was recently separated and Jeff was the first man I'd dated in almost twenty years. I told him that.

"Uh oh," he said, raising an eyebrow. He brushed a strand of hair out of my face and smiled. "I guess I should ask where you are in your life, right?"

"I'm right here, right now," I said, laughing, as I rubbed his arm. "And I sort of like this place. A lot."

There were other questions that I didn't ask: 'Would I have liked them? Would they like me? And why did this matter to me?' As Jeff and I lay together and talked, my mind wandered. Thinking about his exes, I imagined how my life could have gone differently. I wondered what it would be like to try on an alternative life (and the men that might possibly have gone with it), like a pair of Levis. What if I hadn't married my college boyfriend? What if I'd done something other than teach? What would my entire life had been like if I'd chosen a different path? I shut my eyes and pictured alternatives:

Me as a successful businesswoman, focused on my career in banking -- no, corporate law! -- meeting a series of businessmen for a quick wine spritzer after work. The men I date -- power brokers in their fields! -- have to have a greater net worth than me, and I'm very successful. (I'd tried dating a Ph.D. student once -- a nice guy and extremely attentive in bed -- but I'd had to pay for almost everything.) After yet another drink and scintillating talk of mergers, I catch a cab to my prewar classic six on the Upper East Side, stash my imaginary briefcase under the mahogany desk in the home office, and ... I feel a very real nausea wash over me. Even in my imagination, I dislike Business Sue.

Instead, I pull on a black beret, tuck a cigarette behind my ear and move into a small walk-up studio in the East Village. (In my dream life, it's 1986, and the East Village is still affordable.) I paint tiny canvasses with an eyelash brush or make jewelry from gold macaroni. (I relax a bit; this fits better.) I only date men like me, men who understand the creative process. We talk a lot about the creative process as we drink cheap red wine from chipped stoop sale teacups on my fire escape, dangling our legs over the edge. My love life is complicated. I immediately shoo away the man with the heroin habit. I get into heated arguments with another. We scream, break dishes and make love amid the shards. Rubbing my backside, the fantasy dissolves as quickly as the imaginary relationships do with East Village Sue. She's simply too unstable.

As Jeff reminisces about his earlier life and girlfriends, I wonder if I should've kept my mouth shut instead of asking about them -- I'm jabbed by what I think are pinpricks of jealousy. How could I, a single mom pushing forty, a preschool teacher for goodness sakes, compete with the accomplished, interesting women of his past?

I weave the threads of my self-doubt into an insecurity blanket, pull it tightly over my shoulders, and say, "I've got to tell you, I'm a bit anxious. You've dated all these amazing women. I guess I'm feeling a little afraid."

Jeff held me, looked into my eyes, and said, quietly, "Why? Dating was fun, but lonely. I spent an awful lot of time wishing I'd found someone who made me happy, who made me laugh and kept me interested." He laughed. "I wish I'd met you all those years ago."

Real Sue smiled.

A year or so later, we got married. And now, closing in on fifty, I find there's a comfort in knowing so much about the years before we met. But there's also the small thrill of learning something new about Jeff (like, as a child, he never had a stuffed animal or that Frank Rich once sent him a fan letter) that keeps the relationship fresh. It's newness and comfort rolled into one. And I still love hearing about his girlfriends.

Sue Sanders' essays have been published in the New York Times, Real Simple, Salon, The Rumpus and others. She's the author of Mom, I'm Not A Kid Anymore, a parenting memoir.

This essay first appeared on FullGrownPeople.com.

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