Two months into their relationship, Rachel and Dave were ending an evening at Angel's Share, a romantic lounge in back of a Japanese restaurant, sipping Mojitos with their legs entwined, when the check came. Dave hadn't had time to run to the ATM after treating Rachel to a lobster dinner at Docks, so he asked her to throw in $5. "I was like, 'Yeah,' but I didn't like it," says Rachel, a slim 35-year-old redhead who works as an executive assistant at a head-hunting firm. "Dave always talked about how much money he was making, so I was like, 'Why is he asking me for $5?' "

They first met through an online dating service. In his user profile, Dave, a graphic designer who works for an investment bank, had listed his salary as over $100,000. "It did make a big difference," she admits. "It made me more interested in him as a serious candidate." As their relationship developed, Dave's generosity became part of the dynamic. There was a spur-of-the-moment shopping trip to Bloomingdale's, a weekend at the Soho Grand during a summer heat wave, a trip to Portugal for their three-month anniversary. When Christmas rolled around, Rachel sent Dave an e-mail with a couple of gift options: a body polish and a massage from Bliss or, if that was too expensive, a mani-pedi. "He couldn't decide," she says. "So he got me all of it."

That was then. On a recent night, as they lay across the sleigh bed in Rachel's one-bedroom apartment talking about their future together, Dave confessed that he was starting to get anxious. Raises would be nominal this year, his company had warned, and bonuses would be reduced up to 30 percent. If he lost his job, Dave asked Rachel, would he lose her too?

"Rachel has expectations, and she laid the cards on the table right from the beginning," Dave says. "I would love to get into a period of being more serious, maybe get engaged or move in together, but until I feel like I can offer some kind of security, I won't even suggest it. I've kind of resigned myself to busting my ass for at least another year, and it's slowing down my master plan."

He's hardly alone. all across the city, master plans are being scaled back -- or thrown out altogether -- thanks to a softened economy that has introduced salary freezes and layoffs to a generation of young singles grown accustomed to good times. In a town that one frustrated former trader describes as a "merry-go-round of upgrading," guys who used to treat their dates to weekends in the Hamptons and dinners at Olive's now find that they can barely afford the Olive Garden. And as bonus payouts and stock portfolios have taken a beating, so has the most sensitive financial indicator of all: the male ego.

"My financial security really informs my confidence, and my confidence totally informs my ability to meet women," Dave says later. "If I'm feeling insecure about my finances, I would be less likely to start a conversation with the sexy girl sitting at the bar, whereas if I had $800,000 in my pocket, I might be like, 'Hey, beautiful, how's it going?' "

Before he lost his job last year, Keith was working for a telecom company, making in the high six figures, and dating models. Now he's feeling the recession's effect on his love life. "You're not going to go to the Mercer Hotel and buy $14 drinks when you're collecting unemployment," he says. He still takes dates to Blue Ribbon for sushi, but he won't allow himself to look at the right (pricier, à la carte) side of the menu. Matt, who lost his job at a small Internet company ten months ago, hasn't dated as much since he picked up the check for an ostrich-steak dinner at Paris Commune and literally felt sick to his stomach while counting out the bills. "Now I remember what it's like to be broke," he says with a little laugh. "But what am I supposed to say to a girl? 'Want to go to International Bar and get some $2 Budweisers?' "

Such insecurity is understandable. "What's the first thing you ask someone when you meet them in New York?" asks Ann, whose relationship ended after her boyfriend Darren lost his job as a banker at Goldman, Sachs. " 'What do you do?' I think when a man loses his job, it's the worst thing in the world, because, especially in New York, his identity is so wrapped up in it." Ann promised Darren she would see him through his unemployment, but she soon began to resent his attitude of "doom and gloom." The last straw came two days after Christmas, when Darren's roommate came home, raving about a ski house he had just visited in Vermont. "Darren was getting more and more depressed, saying things like 'I'll never be able to afford a ski house,' " Ann recalls. "It escalated into this huge argument, and finally I said, 'Well, Darren, you're going to have to break up with me if that's where you're going with this, because I'm not going to break up with you.' And out of the blue he goes, 'Fine, let's break up. I can never be enough for you.' I left the house and just burst into tears. I couldn't believe it. I was like, 'What just happened?' "

Thomas, a 39-year-old former advertising copywriter, thinks he knows. "You have to have a ton of money to play the game," he says with an edge of bitterness in his voice. "Women in New York are the first ones to say 'I want a nice guy,' but what they really want is a rich nice guy." Although he saved enough money to live on -- "Thank God" -- it hasn't been enough to cover drinks at the Time Hotel and dinner at Thalia, followed by dessert at La Fortuna. So as far as dating is concerned, he's on the bench. "Jesus, it's been about three months now," he says.

Before Chris lost his investment-banking job at Deutsche Bank, he had gotten used to working 80 hours a week and then another 10 or 20 hours on the weekends -- when he wasn't out in the Hamptons. When he found the time, he would pick up dates in the company car. Now, after spending so much time alone, he wants to go out more. To his surprise, though, many women don't have time for him. "You say you're between jobs, and they give you that look," he says. "There's the sympathy look, and there's the 'I need to end this conversation so I can move on to the next guy' look."

On a recent Friday night, Sascha, a petite 25-year-old blonde in a $400 Donna Karan top, is parked in front of the velvet rope outside Pangea so the bouncer can get a better look at her. "I wouldn't date a guy who's unemployed right now, period," she says. "I won't just settle for a guy who's nice and treats me well -- I want to have a good life." Weekend after weekend, she pulls on her Sigerson Morrison boots, applies makeup between her breasts to enhance her cleavage, and hits upscale clubs like Bungalow 8 and Lotus. When a guy hits on her, the first thing she does is check out what he's wearing -- his shoes, his watch. Then maybe she'll allow him to buy her a drink, or else she'll give him the Look.

The last time Sascha was at Pangea, she stepped outside to check her voice mail and a tall, blond Italian guy told her she was beautiful. On the way back in, she gave him a playful tap with her handbag. They started to dance, and he asked her out. "Right away, I'm thinking, 'Who is this guy? What does he do?' " she says. "He wouldn't tell me, but I was like, 'Fuck it, he's cute, I'll go out with him.' " The next night, they returned to Pangea, where a friend of Sascha's recognized her date -- as a waiter at the Park. "I was like, 'It's over,' " says Sascha. "I went back to him and said, 'I know what you do.' I'm sorry, but I have ambitions in life. I can't date a fucking waiter. I have a friend who's unemployed right now who always wants to take me out, and I'm like, 'No, you can't afford me.' "

Which, of course, isn't necessarily a bad thing. "When you were working, you might have dated a hot girl who wasn't a good person," says Ethan, a 33-year-old former marketing director who lost his $90,000-a-year job in the fall. "Now you're like, 'I've got bigger things to worry about than going on a date with you.' " Over New Year's, Ethan went to several parties and discovered there were more people in his situation than he'd thought. "Money is no longer an issue," he says, "so you start to search for what you really want in someone. When I was working, I didn't think twice about dropping $200 on a date. Now, instead of taking someone to Man Ray, I might say, 'How about a movie?' " He pauses thoughtfully. "Any jerk can take you to Man Ray," he says. "It's the easy way out."

From the February 11, 2002 issue of New York magazine

Photo: Brian Velenchenko