Matchmaker, Matchmaker

Looking for a date this Valentine’s Day? Skip in favor of Highland Park’s Jill Rudman.

Jill Rudman of Highland Park is a professional matchmaker, but she’s so genuine and down to earth she seems more like a cool new girlfriend who just happens to know the perfect guy for you. And that’s just how she wants people to feel about her.

“The best way to meet someone is through a friend,” she says.

When working with a client, Rudman becomes that friend—but with one important difference.

“I’m completely on your side,” she said. “I want this to work out for you.”

Rudman got into the matchmaking business because she’s a natural. She’d been successfully fixing up her single friends for years before launching her career as “Ms. Matchmaker” last January. Married with four kids, she’s not on the market herself, which makes her all the more objective when it comes to relationships.

Rudman works with men and women from all over Chicago and the North Shore. Her clients’ ages range from late 20s to 75 years old. They might be looking for different things, but they all share common traits.

“My clients are active, successful people who have friends and go out on dates,” Rudman says. “My services are supplemental to the social life they already have.”

Rudman meets prospective clients and screens them simply by sitting down and having a good, long talk. If she feels she can help, you’ll sign a one-year agreement for fee of $1,200. Which is actually quite cheap compared to other dating/introduction services in the area. For that fee, Rudman guarantees at least five dates.

Her focus is on quality dates, and she looks far beyond her own client pool to find them.

So, what makes a good match?

“It helps to start a relationship when you have a common ground to work with,” she says.

She believes people with the same type of backgrounds, interests, values and ages (sorry, cougars) are the most likely to hit it off.

As we were chatting, Ms. Matchmaker received a text message from one of her male clients. She glanced at her phone, smiled and read the message aloud:

“I’m seeing her for the fourth time since Friday. We are getting along quite well.”

“That just makes me so happy,” Rudman says while beaming, obviously thrilled. “I love it!”

Ms. Matchmaker’s Rules for Women on a First Date

1. Dress tastefully. Men like women who take care of themselves and make an effort, but they don’t respond to women who appear sleazy. Don’t show too much skin or slather on the make-up. Guys find this intimidating.

2. Be positive. Talk about the good things in your life; be interested and upbeat. By no means bash your ex or discuss personal problems. It’s way too soon.

3. Act like a lady. Don’t drink too much, smoke too much or use foul language. It might be fun, but this early in the game, it’s a turnoff.

4. Give the guy a chance. Jill has had clients tell her, “he was so close, but we had no spark.” Sometimes it takes a couple dates for attraction to develop—if you like the man as a person, stay open.

5. Finally, be kind. Even if you’re 100 percent sure there is no future, you still want your date to leave having had a nice time. You might bump into him again, and who knows? He might have a friend or a brother.