As a single guy in New York, I meet all kinds of different women; on any given weekend, I might meet a serious financier, a flighty stewardess, an intellectual grad student, a bohemian textile designer, whatever — and I have! Some of my relationships with these women have lasted several years, others just a few weeks. And though I’m constantly refining what sort of woman I’m searching for, some of my best dating experiences were with those who I would have sworn weren’t remotely my type. I had fun, sure — but more importantly, I gained some important insight into myself and my love life. Here are some of the surprising types of women I’ve dated, and why I’m glad I did:

1. The daddy’s girl
Think that “daddy’s little princess” is the last kind of woman you need to date? Well, listen to this: Maria, a 25-year-old grad student I met online, surprised me on our first date by divulging that she lived with her parents. What’s more, she worked at her father’s law office. It quickly became obvious that she was very close to her father, a man who paid for her food, clothes, taxis — everything. After a few weeks of seeing each other, Maria took me home to meet her folks. As I’d anticipated, her dad was Robert DeNiro-level gruff upon receiving me, but warmed up when I presented his wife with a bouquet of lilies. While Maria helped prepare dinner, I chatted with her dad, trying my best to impress him. Maria and I left that night emboldened by my seeming success in wowing her father, who invited me back “anytime I wanted.” My relationship with Maria progressed, and I spent more time with her — and her family. Soon I was enjoying weekends at their beach house and home-cooked meals. More significantly, I came to see Maria’s dad as a surrogate for my own father and looked to him for career and life advice. When Maria and I broke up, I considered how disappointed he would be with me for failing to take care of his little girl. Still, I knew she had him to go to for support post-breakup.
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What I learned from dating her: Dating a woman who is close with her father means you are also going to become close with him. I was proud to win over Maria’s dad and be entrusted with his “little girl,” but post-breakup, I realized that I had been overeager to be a part of a family and not excited enough about being in a relationship with Maria. Maria, on the other hand, was more into gaining her father’s approval than she was into me. Ultimately, I learned that I should want to be a good boyfriend more than being a good son — at least, not to anyone but my parents.

2. The surrogate mother
I am (and have always been) close to my mother. I rely on her for support, advice, and the occasional pampering — a bowl of hot soup and permission to veg out and watch Big on DVD when hom sick on the couch. My college girlfriend Amy was caring, nurturing, responsible — and reminded me a lot of my own mother. Our relationship evolved from friendship into something more, and I took advantage of Amy’s focused attention on me by unloading my daily stresses and getting her to help me with nearly everything. When I wasn’t feeling well, she’d bring me lemon tea with honey. When I needed a ride, she’d drive (or let me borrow her Eclipse). When I suffered a disappointment — like being wait-listed for a foreign teaching job I’d applied for — she was sympathetic and encouraging. It seemed that all she really wanted from our relationship was for me to be happy... just like mom.

What I learned from dating her: Being with Amy was comfortable, and being comfortable enough to be myself with someone I’m dating is an ongoing challenge. We were content to spend hours indoors talking, studying or watching TV together instead of partying, so she was definitely a calming influence on me. But I could never envision Amy and I truly exciting each other throughout our lives. I broke up with her using an awful cliché, which was unfortunately apt: “I love you, but I’m not in love with you.” Sadly, it was the truth.

3. The struggling artist
I couldn’t help but flirt with Nadia, the beautiful waitress at the upscale joint where I was hanging with my friends one night, and ask her for her number. On our first date, Nadia mentioned that she worked as a waitress to pay rent, but that her real passion was her art. She was a trained painter and sculptor who worked primarily with glass. Being with an artist — someone who devoted all of her available time and energy towards creating works of art — humbled and inspired me. As a writer, I’ve always felt I could do more to “create,” perhaps by crafting a thoughtful short story or even a novel. My horizons expanded, too, as I took Nadia on cultural dates, splurging on museum admissions and concert tickets for us both. She never offered to chip in — but I was fine with that, equating “struggling artist” with “starving artist.” Plus, paying made me a gentlemanly patron of the arts! I didn’t really “get” her stuff (half-glass, half-leather structures, mostly), but by the time she showed it to me, I was too into her to be much of a critic. Unfortunately, Nadia was far more into her work than she was into me, and she’d spend what little time she had away from her job at her studio space. I felt lucky if we hung out more than a few hours each week.

What I learned from dating her: Passion is sexy, and few women are as passionate as working artists are. And though her passion wasn’t always extended to me — I did all the pursuing, calling and planning when we dated — she was wholly engaged when we were together. Seeing the artistic glint in her eye was more than a turn-on — it was an inspiration. But being someone’s second priority (or lower), even if her first priority is art, wasn’t what I wanted — I wanted Nadia’s passion focused on me. And I learned that with a dedicated artist, that attention just isn’t always in the offering.

4. The older woman
“You and Michelle will totally hit off,” my matchmaker friend Katie told me. “Oh, and she’s a few years older than you,” she added, figuring it wouldn’t matter to me. I didn’t think it would, but I was still taken aback when I met Michelle. At 40, Michelle was 12 years my senior — and what a difference those years made! I have nieces; she had a four-year-old. I rent an apartment and have roommates; she owned her place. My longest relationship lasted three years; her marriage lasted… OK, so at least in that regard we were similar. But within minutes of hanging out with her, Michelle had shattered all my assumptions about single moms being exhausted and stressed out all the time. Instead, Michelle was funny, insightful and successful. Michelle had founded a national magazine I was familiar with; what 28-year-old could claim such an accomplishment? On our dates we talked about travel, work, friends we had in common, and all the other stuff two people talk about when they’re getting to know each other. Naturally, she spoke about her daughter a fair amount, but not in such a way that I felt like she had no social life. On the contrary, we met up for movies, dinners, late-night improv comedy shows — anything we liked, really, so long as she had a heads-up in time to find a sitter.

What I learned from dating her: Prior to dating Michelle, I gravitated towards girls my age or younger, like most guys do. But being with Michelle made me realize that an older woman has several advantages over her younger competition — she’s confident enough to realize that other women aren’t her competition, for starters. Michelle had done a lot in the years between her mid-twenties and thirties, and she oozed sophistication and confidence. Being with her earned us looks, but I hardly noticed them, so entranced was I in every bit of wisdom and insight she imparted to me. And the few years she had on me didn’t make her a laggard in the fun department. Though our chemistry failed to boil over into something more serious than casual dating, we still hang out and she still impresses me with her vitality and independence — qualities I would want in anyone I date.

5. The wallflower
Opposites attract, right? Such was my thinking as I dated one social gadfly after another, hoping their life-of-the-party ways would rub off on me and I’d become more fun by association. Until I met Elizabeth, that is. Like me, Elizabeth was serious, an avid reader — and painfully shy at parties. It should come as no surprise that we met online, two homebodies now enabled to find each other thanks to the Internet. We both preferred spending Friday and Saturday nights somewhere quiet sharing a conversation or at my apartment playing card games to hitting up as many happening spots in the city as we could find. We did occasionally end up at parties or other shindigs where I would be content to bring her refreshments before we’d once again retreat to a corner to chat privately amongst ourselves.

What I learned from dating her: Especially early on in relationships, I tend to cater to my dates’ “fun” sides, whisking them from pre-party to special event to concert to party to after-party, all in the hopes of seeming spontaneous, exciting, and in-the-know socially. Elizabeth’s awkwardness in such settings was something of a relief, since I didn’t need to prove how well I could work a room just to impress her. And she had little interest in going out (and much less in partying), so I became better able to skip those exhausting long nights out guilt-free and instead learned to appreciate quiet nights in — with someone who liked to play cards! We broke up shortly after I met Nadia (see “The struggling artist” above), so perhaps I need someone a bit more exciting. But I did learn that dating needn’t be all about going out and getting crazy; there are quieter pleasures to be had, too.

6. The girl who’s smarter
I pride myself on my word knowledge, and I am also a very sore loser. How, then, could I control myself every time Laura beat me at Scrabble by playing nine-letter words like “ideations” (which is a fancy term for “thought” — I had to look it up)? Laura and I both went to the same small liberal arts college and both majored in English literature, but while I’ve spent the years since then flipping through magazines I hoped to write for and recording cartoons on my DVR, Laura continued to study, earning her Master’s degree before moving to New York to begin work on her Ph.D. Dates with her were far more diverse than what I’d grown accustomed to. Rather than talk about the NFL or see a movie, we discussed narrative framing in William Faulkner’s works or the difficulties inherent in a representative democracy (or something we’d both read in that week’s science section of the New York Times). But I always felt like she was holding something back, afraid of referencing a work of romantic poetry (her subject of study) for fear it would go over my head — which would have been the likely result.

What I learned from dating her: Having conditioned myself to not seem too smart on first, second, and even third dates, I was likely projecting my own embarrassment about being smart onto Laura — when, in fact, she had no such qualms about her own intelligence or about being more scholarly than I was. I loved that she understood what I said when I was making sense — and would even try to keep up with me when I didn’t. And though I didn’t start reading Milton because of Laura, I still appreciated that she could talk about his writing intelligently and in such a way that even I could understand it. (She’s on her way to becoming a professor, after all.) Though we’ve reverted to being “just friends,” I still hang out with her for the stimulating conversation — which is evidence of the mental gymnastics I have now come to expect on a first date, both from the woman I’m with and from myself.

So, while none of these types turned out to be the right type for me, I am grateful for having dated each of them — and for the lessons they’ve taught me as I continue to look for The One.

Matt Schneiderman has written for Stuff and Giant.