My first test for dating is my intuitive level of comfort with someone. When I’m comfortable, it’s easier for me to be honest, and for her to be honest, and everything just works easier that way.
I usually feel quick rapport, for instance, with Dennis Prager fans, with certain Orthodox Jews, with writers, with converts, with people from the British Commonwealth. I particularly get along with the English, South Africans, Australians, Kiwis, etc.
How much money will I have to spend on her? I’ve always been poor. I’ve never made more than $50,000 in a year, so this is a big deal. Logistically, I just can’t go out on the town a lot. I had this one beautiful girlfriend, she might’ve been an eight on a one to ten scale, and she was ten years younger than me and from Malibu. She was the most beautiful girlfriend I’ve had and she was also the most demanding. We could rarely just hang out. Instead, I had to take her out. Usually it was to dinner and a movie, but sometimes it was to museums or to parties. And the next morning, she’d want me to take her to breakfast (which I never did).
When we went to swanky parties at flash hotels, she’d want me to book us a room. I never did because of the expense. No other girlfriend made such requests on me.
I would not call her materialistic nor a gold digger. She dated me even though I drove a battered car and lived in a hovel. But for my limited means (I was earning about $42,000 a year at the time), she was expensive.
I wouldn’t call her high maintenance. She didn’t expect constant gifts and compliments and support. I only sent her flowers once (that was after our first time, and the card I sent said I loved her, and she told me it was too early to talk about love, and so I never again sent her flowers, then she told me months later how much they meant to her, though at the time she just took me down a peg).
My male friends were jealous of me for dating her and several of them hit on her and got rejected. I could see in their eyes how they longed to do the things with her I was doing.
One guy was my good friend who was also her boss. Then I heard from her how he’d hit on her and she rejected him. I didn’t hold it against him, but ever since, he won’t be my friend, not even on Facebook.
“She looks like the type of girl who’ll let you do anything to her,” said a jealous older woman to me.
My, did the old bags hate her.
Because she was cute, she was used to getting her way. I remember one time when she had the flu and was staying in Malibu, she asked me to drive about 25 miles to bring her soup and crackers. That would’ve required me to skip an LA Press Club event. I said no.
She found that devastating and broke up with me the next day. Because she had broken up with me several times before this, I was not inclined to go the extra mile to bring her soup and crackers. If we had never broken up, I would’ve done it, knowing I had a loyal girlfriend.
She expected that if I wanted to win her back and to keep her, I should care for her in this manner. When I didn’t, it felt like a stake through the heart.
She called her ex-boyfriend and he immediately dropped work and drove out to her, bringing soup and crackers.
I’ve never had any other girlfriend make such a request. They know I’m selfish and don’t try that stuff.
I don’t think I’ve ever asked a girlfriend to bring me anything when I was sick. Only when they asked if I needed anything, and then I sometimes said I’d appreciate some company or some soup or some such.
Another key factor in determining how much trouble somebody will be to date is if you’re seeking the same type of relationship (per Alison Armstrong). Some people primarily want a legacy relationship — they want to leave something behind like children.
People like me primarily want a companionship and personal growth relationship. Others primarily want a relationship revolving around support for each other’s cause such as religion or animal rights.
Another factor is, does the person see you for who you are or for who you represent? For one of my girlfriends, she saw me primarily as a representative of Orthodox Judaism. As she hated Orthodox Jews, we were doomed.
One of my girlfriends had contempt for men. Her father screwed around and this caused her hell growing up. So she hated men. And had contempt for me. When I complained that my feet hurt me because of plantar fascitis, she’d say, “Do you want me to airlift you out?” When I said I was exhausted from Chronic Fatigue Syndrome, she’d say, “You seem to me to have lots of energy to me (implying my CFS is all in my head).”
The more attractive the woman, the less effort she’ll put out. She’s used to men going out of their way to please her and she takes this for granted.
Chris Jones writes in Esquire:
On the spectrum of male lovers, I believe I would fall somewhere between “not totally unpleasant, but not totally pleasant, either” and “adequate.” I have a lothario friend, well endowed and blessed with an almost sociopathic stamina, and I know the women who crowd around his door like cats leave more satisfied than I’ve left women even in my dreams. I know that because I’ve literally heard the words “Let’s get this over with.”
And yet I can still say with confidence that there are women who are worse in the sack than me. I’ve slept with you: unenthusiastic, uncomfortable, and uncommunicative, the human equivalent of the space between the couch cushions, only without the bonus possibility of my finding loose change in there. That’s only natural, of course. There is a spectrum of female lovers just as there is of men. The trouble is, most women act as though they’re sexual Olympians, as though they’re doing the men in their lives the greatest of favors merely by presenting themselves like a downed deer strapped to the hood of a car. Some of you are deluding yourselves. Sex is not like pizza. Only blowjobs are.
