The Deal-Breakers

The woman who made Bill O'Reilly look polite
Sometimes the date that seems too good to be true really is. "My friend hooked me up with a friend, and when I met her for our first date, I couldn't believe she was single. She was gorgeous," says Jordan, a 29-year-old teacher from Toronto. But then they were seated… "She immediately got snippy with our waitress. There was a smudge on her fork and made a really big deal about getting one that 'wasn't already used.' Over the course of dinner, she sent back two glasses of wine before she found one pleasing enough to her palate and then loudly whispered a nasty joke about this heavy couple next to us sharing a dessert. I suddenly realized why this beautiful woman was single. That check could not have come fast enough."

The woman who would be my mother
"OK, I'm not the tidiest person in the world," says Patrick, a 29-year-old journalist in New York. "But I don't leave dirty dishes around or anything. Just a lot of clutter. Well, I went out with a woman my co-worker set me up with. When we went back to my place for a drink, she took one look at my apartment and gasped. Then she said, 'How do you live like this?' In an instant, this attractive woman morphed into my mom, and I felt like a pissed-off teenager. I half-heartedly offered an apology, told her I was tired and offered her $20 for a cab."

The woman who was about to go postal
"I met a woman through a friend who seemed cool," says John, a 35-year-old sales manager from Chicago. "Our offices were close, so we decided to meet up for coffee on a Friday afternoon. After we sat down, I made the mistake of asking, 'How do you like your job?' She went off for fifteen minutes straight about how her boss was out to get her and her co-workers were all a bunch of backstabbers. I mean, I felt bad for her, but I wasn't even three sips into my latte before she started unloading! I wondered if maybe she was the unstable one in that workplace!"

The woman who had a skeleton in the closet
"I had the craziest date a few months back," says Rich, 32, a graphic designer from New York City. "It was the third time we had gone out and at the end of the night, she asked me if I wanted to go back to her place. We had just started kissing in her room when we heard the front door open and a dude call out her name. She froze in terror and, I am not lying, whispered for me to hide in the closet. I was so confused, and maybe a little buzzed, that I actually got in her walk-in closet! I sat there for what seemed like forever listening to them fight. From what I could tell, they used to live together and broke up, but obviously hadn't worked everything out yet. The guy eventually left… and I was not far behind him."

The Deal-Sealers

The woman who could have fun at a funeral
"It was only my second date with Jane when I thought: This could be it," says Ed, a 32-year-old CPA from Michigan. "And it wasn't because anything spectacular happened—it was just the opposite. First, I was 20 minutes late to pick her up, then I got lost trying to find the restaurant. Our table had been given away by the time we got there, and instead of eating at this nice restaurant, we wound up at Wendy's. A lot of people would be so peeved, but she just laughed it off! Three months later, she's still refers to Wendy's as 'our restaurant.'"

The woman who had a deep love of cheese
Seth, a 28-year-old engineer from Atlanta, felt his heart skip a beat over the world's most unlikely love song. "My buddy needed an extra player on his company's softball team, so I filled in. I got to talking to this cute girl on his team. Later, at a bar, Huey Lewis came on the radio and she started singing every single word to 'Stuck With You.' I am such a closeted Huey fan that I was like, I have got to ask this girl out this second. I did, and we've been going out for a year now."

The woman who outclassed me
"On our first date, Lori and I took the subway," says Rob, 31, a banker from Brooklyn, New York. "We were sitting side by side, talking, when suddenly she jumped up and told this older woman who was weighed down with shopping bags to take her seat. I hadn't even noticed the woman! Of course, I then gave Lori my seat. It was just a small gesture on her part, but it showed what kind of person she was. And that she was someone I'd be psyched to call my girlfriend."

The woman who played vet
"The second time I went out with Beth, we never actually made it out of my house," says John, 35, a management consultant from Los Angeles. "We had dinner reservations near my place, so she came by to pick me up. Well, before we could get out the door, my dog got sick all over the kitchen floor. She helped me clean it up, but then he took a few steps and got sick again! Most people would have taken that as their cue to leave, but Beth stuck around while I talked to the vet and insisted on accompanying me to the emergency clinic. It was so incredibly sweet. My mutt pulled through, and I knew I had lucked into something very special."

Will Scott is a writer in New York City. His deal-breaker? Women who talk politics so much they turn the first date into an episode of The McLaughlin Group. For the other side of this story, read Her Deal-Breakers...and Sealers