EILEEN MINTZ is the founder of Mintz Media, a public-relations firm specializing in restaurants. She's had matchmaking inclinations "from the time I was a teen, matching friends," she says, and continues to pair up people she knows with (hopefully) suitable mates—but only if they ask her to.
How to ease the pressure of a first date: A shared activity. "An activity allows you to start being yourself. It allows you to partake in something that brings you joy, so you're already in a good mood."
Where to go on a first date: A picnic date at Green Lake, a ski date ("if money is not tight"), or a play followed by coffee. "I truly believe the best thing one can do on a date is not only have a shared activity but make time to talk."
What kind of small gift to bring your date: Something based on your first conversation(s). "Showing that you are a good listener means finding an article that relates to one of the passion[s] your date is interested in, such as a New York Times article about a chef, if she loves cooking. Flowers are meant for a second date or if invited over for a meal, and they should be something like freesia, [which] have a fragrance to remind your date of you!"
How to really get to know someone: Spend a full year together. "You should see each other through different seasons. I think every season you're a little different."
Some factors involved in making a match: Character, financial habits, and neatness. "In essence, when you get to know somebody really well, you're going to think about how you're going to live together."
A tip on Internet dating: Don't move too fast. "You become very intimate faster on the Internet than any other way. And you're thinking of it as love, but it really is lust. Love develops. Love grows deeply with give-and-take and time spent."
Advice for aspiring matchmakers: Work only on demand. "Don't do it unless you're asked. Don't butt into other people's lives. That [is] my best advice."