6 Types of Women You Should Date and What You Might Learn from Them

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.

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…

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