The 5 Women You Must Date…

Our writer says these surprising types are definitely good to go out with.

By Matt Schneiderman

s 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 my type. I had fun, sure, but more importantly I gained 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 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
Date a daddy’s girl? Yes, you should.
online, shocked 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 De Niro gruff upon receiving me, but warmed up when I presented his wife with a bouquet of lilies and a bottle of wine. 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.

What I learned: Dating a woman who is close with her father means you are going to become close with her father. 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 eager enough about being in a relationship with Maria. Maria, on the other hand, was more into her father’s approval than she was into me. Ultimately, I learned that I should want to be a good boyfriend and not a good son—at least not to anyone but my parents.

2. The struggling artist
I couldn’t help but flirt with Nadia, the beautiful waitress at the upscale bar where I was drinking with friends one night, and ask her for her number. On our first date, Nadia mentioned that she worked as a cocktail waitress to pay rent, but that her real passion was her art. She was a trained painter and sculptor and 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 craft a thoughtful short story or, even, a novel; perhaps I was Gertrude Stein to her Pablo Picasso—but straight and dating each other. My horizons expanded, too, as I took Nadia on cultural dates, splurging on museum admissions and concert tickets. 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-animal-gut 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 the bar at her studio space. I felt lucky if we hung out more than a few hours each week.

What I learned: Passion is sexy, and few women are as passionate as working artists. And though this passion wasn’t always extended to me — I did all the pursuing, calling and planning — she was wholly engaged when we were together (and that included the most intense sex I’d had in years). 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 in the offering.

3. 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
Artists are among the most passionate women out there…
longest relationship lasted three years; her marriage lasted… OK, so at least in that regard we were similar. But within minutes of our hanging out, Michelle had shattered all my assumptions about single moms being exhausted and stressed out. 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, our 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, drinks, late-night improv comedy shows—anything so long as she had a heads-up in time to find a sitter.

What I learned: Prior to dating Michelle, I gravitated towards girls my age or younger, like most guys. But being with Michelle made me realize an older woman has several advantages over her younger competition—that she’s confident enough to realize that other women aren’t competition, for one. Michelle had done a lot in the years between her mid-20s and 30s, and she oozed sophistication and confidence. Being with her earned us looks, but I hardly noticed them, so entranced was I with 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 from anyone I date.

4. 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, homebodies now enabled to find each other thanks to the Internet. We both preferred spending Friday and Saturday nights at a quiet bar with Guinness and conversation or at my apartment playing gin rummy—rather than 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 drinks before we’d again retreat to a corner to chat among ourselves.

What I learned: 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. Elizabeth’s social awkwardness was something of a relief, since I didn’t need to prove how well I could work a room to impress her. And she had little interest in going out, much less in partying, so I became better able to skip exhausting long-nights-out 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.

5. The girl who’s smarter
I pride myself on my word knowledge. I am also a very sore loser. How, then, could I control myself every time Laura beat me at Scrabble, playing nine-letter words like IDEATIONS (a fancy term for “thought” —I had to look it up)? Laura and I both went to the same small liberal-arts school and both majored in English Literature, but while I’ve spent the years since college flipping through magazines I hoped to write for and TiVo-ing cartoons, Laura continued to study, earning her master’s degree before moving to New York to begin work on her Ph.D. Dates 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 Faulkner 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 back, afraid of referencing a work of romantic poetry (her subject of study) for fear it would go over my head—which was the likely result.

What I learned: Having conditioned myself to not seem too smart on first, second, or third dates, I was likely projecting my own embarrassment about being smart onto Laura—when, in fact, she had no such qualms about her intelligence or about being more scholarly than I am. 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, I still appreciated that she could talk about his writing intelligently and in such a way that even I could understand her. (She’s on her way to becoming a professor.) Though we’ve reverted to being “just friends,” I still hang out with her for the stimulating conversation—the evidence of mental gymnastics I now come to expect even (or especially) on a first date, both from the woman I’m with and from myself.

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

Matt Schneiderman has written for Stuff and Giant magazines.

For the other side of the story, read 5 Guys You’ve Got To Date.

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