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Let’s hear it for the girls.

For the first time, women in their 20s are making more money than their male peers in Chicago and other big cities, thanks in large part to more women than men getting college and advanced degrees.

Now for the bad news. These same twentysomething women also are in prime dating mode — and their financial superiority doesn’t always go over well with either sex in the hunt for a mate.

Latesha Lipscomb, 29, said she has dated plenty of men who earn less than she does, and “it’s becoming more of an issue.”

Lipscomb, who lives in the South Loop, said she makes about $70,000 a year juggling a full-time job as a paralegal, a part-time job as a makeup artist for Mac cosmetics and the occasional gig as a full-figured model. Dating has gotten “very frustrating,” she said, as she navigates fragile male egos that are intimidated by her accomplishments and seeks to satisfy her own expectations that men live up to her expensive tastes.

Lipscomb said a former boyfriend balked when she suggested they spend a weekend at the W Hotel because he thought it was a waste of money.

“I want someone who wants to take trips to wine country,” Lipscomb said. “You need to come to the table knowing that I want to go to Jamaica for my birthday.”

Nevermind that Lipscomb herself could afford a trip for two to Jamaica.

“I’ve come to the conclusion that if I have to pay for you, you ain’t a man,” she said.

As much as women strive for financial independence, convention often trumps feminism in the dating world, where the man still is expected to be the dominant, or at least equal, partner.

That gets tricky when women make more money than their dates — which is happening among twentysomethings in several cities including Chicago, New York, Minneapolis and Boston, according to an analysis of 2005 Census data by Queens College Sociology Professor Andrew Beveridge. >>

In Chicago, full-time working women between 21 and 30 made a median wage of $30,560 in 2005, 7 percent more than the $28,523 earned by their male counterparts, the analysis found.

“This is new, having significant numbers of women in their dating years making more than men,” said Barbara Risman, chair of the sociology department at the University of Illinois at Chicago and an executive officer of the Council on Contemporary Families. She said the female income supremacy is likely a “phenomenon of youth” that will not carry into the 30s because once women become mothers, they usually reduce their working hours and lose pay.

While the income gap usually doesn’t harm established relationships, courtship — a time fraught with misunderstanding — can be strained as women who can afford a certain lifestyle date men who can’t, Risman said.

“We all have these gender expectations that are really about how people see themselves as effective men and effective women,” she said. “When you have a pool of eligible men who are not doing as well as women, the men may feel they’re not meeting the expectations and women might feel that way as well.”

Money insecurity once got in the way of Lisa Ditkowsky’s relationship. Ditkowsky — now 32, married and living in Evanston — remembers being 27 and working two jobs while she dated a guy who was “sporadically employed in the creative arts.”

“He was very jealous and insecure that I would leave him for someone with money,” Ditkowsky said. “He got jealous when I decided to become a stock broker.”

Ditkowsky, now a financial planner and president of Pllush Capital Management, said that what got to her more than her boyfriend’s lack of money was his lack of ambition. His goal, she said, “was to be Mr. Mom someday,” and at 29 he still had student loans and creditors after him.

Even women who don’t mind making more money than their mates still want to feel like they’re being treated every once in a while.

Tanalee Theanchai, an accountant who lives in the West Loop, is a big fan of eating out, but she dated a man for many years who didn’t like to spend money on fine dining. He made $20,000 less than her a year, she said.

While Theanchai appreciated his frugality, she felt deprived.

“It would be nice to have something nice every once in a while, to feel that he was making an effort,” said Theanchai, 32, who ended the relationship for different reasons.

For J.T. Thomas, a 28-year-old bartender who lives in Wrigleyville, getting past the income gap is more about effort than money. Thomas expects that he will soon be making less money than his girlfriend, who is getting her master’s degree in early childhood education, but he isn’t worried he’ll let her down.

“You can do something equally nice but not as extravagant,” he said.

Other men are more conflicted.

Tim Straub, a 27-year-old bartender who lives in Lakeview, said he once dated a medical school student whom he knew would eventually make much more than he does.

“It caused stress in my mind, because I wanted to feel like what I was doing would be equal to what she contributed,” Straub said. “You do want to fulfill the ‘man’ role, even if the role is socially contrived.”

Dominic Wayne, a 28-year-old DJ from Rogers Park, said he used to date an accountant who insisted on paying for everything. He didn’t mind — until she used it to criticize him.

“It didn’t bother me how much money she made, but I didn’t like that she’d be like a mother and throw it back in my face,” Wayne said.

Oftentimes, women say, dating frustration is less about mismatched incomes than mismatched drive.

“It’s difficult to find a guy who’s your equal, who’s not intimidated by you and is not going to hold you back or feel threatened,” said Freda Mooncoch, a 35-year-old Gold Coast resident who said she made about $20,000 to $30,000 per month running her own mortgage company before she launched alphawomen.com, a Web site for professional women to discuss issues of life, love and work.

Lipscomb said she used to tell men only that she worked for Mac cosmetics, and not mention her law degree, to keep them feeling superior. But now, she said, she refuses to date any more “community service projects.”

“The dumbing down days are over,” Lipscomb said. “Life’s too short.”

– – –

Making the most out of all that cash

Forget relationships with men. Some women who make a pretty penny have a tough enough time relating to their own money.

Young women typically are not as good at saving or investing their money as young men are, and women are more prone to spending everything they make, said Lisa Ditkowsky, president of Pllush Capital Management, a financial planning firm.

“What worries me about young women who are making all this money is that they aren’t going to have anything to show for it in five years,” Ditkowsky said.

“Young male clients seem much more motivated to save and invest than women,” probably because many have been raised to think financial planning is a man’s job, she said.

Women who do save tend to be more risk-averse and play it safer than men, putting all of their money in CDs instead of investing more aggressively, said Tiffany Bass Boukow, founder of www.msmoney.com.

“We see that women’s financial returns are less than men’s,” Boukow said.

To make the most of their earnings, Ditkowsky said, women should get free consultations from at least three financial advisers, asking lots of questions about fees and risk in order to become more comfortable with the concepts and choose an adviser wisely.

Controlling the checkbook might also lighten the angst of dating men who earn less, Ditkowsky said.

“If you have your investment life under control, you’re not going to see yourself as so rich compared to him, because that’s just money for the future,” she said.

— Alexia Elejalde-Ruiz, RedEye

Income not an issue for this area couple

With an annual salary of $160,000 plus bonus, attorney Emma Rodriguez-Ayala makes more than three times what her husband, Eric Chitwood, makes at his IT job.

Rodriguez-Ayala, 25, said she expects to continue to be the breadwinner even if the couple has children, with Chitwood, 27, staying home with the kids — a notion that’s causing some consternation among their parents.

But the Hyde Park couple, married for four years, doesn’t think the gender-role reversal matters one bit.

“Eric and I are 100 percent equal partners in our relationship,” Rodriguez-Ayala said. “He does all the housework and cooking, which more than makes up for his lower salary.”

“It’s perfectly fine for me,” Chitwood says. “She enjoys what she’s doing, and I enjoy what I’m doing.”

That attitude is thanks in large part to the fact that the couple met when they were both broke college students in Missouri, Rodriguez-Ayala said. Chitwood supported her while she went to law school, so they feel they’ve shared the financial burden, and all their current earnings are communal.

— Alexia Elejalde-Ruiz, RedEye

– – –

By the numbers

7%

How much more working Chicago women in their 20s make than their male counterparts.

11%

How much less working women in their 20s nationwide make than their male counterparts.

23%

How much less women in all age groups nationwide make than men.

35.6%

of working women in their 20s have college degrees, compared with 22.7 percent of men.

33%

of married women earn more than their husbands.

35%

of single women have retirement accounts, compared with 42 percent of single men and 62 percent of married couples.

84%

of very rich women say having money means having better sex, compared with 63 percent of rich men who said the same.

[ Sources: Queens College analysis of 2005 Census; 2006 Census; Bureau of Labor Statistics; Federal Reserve; Prince and Associates, a market research firm focused on private wealth ]

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aelejalderuiz@tribune.com