A Matchmaker's COMPLETE Guide To Totally Acing The First Date

Best. Advice. EVER.

By Erika Gershowitz

With all the apps and online dating options we have these days, scoring the first date is easy. But making it to the second date? That's where it gets complicated.

Since first dates are so tricky to navigate, we've decided to enlist the help of a professional. Erika Gershowitz is a Three Day Rule matchmaker in NYC and she's mapped out the ultimate Do's and Don'ts for all you daters out there. What is the Three Day Rule? Basically a "white-glove," personalized matchmaking company backed by Match.com with a team of experts located across the country. Interested in a personal dating concierge? You can sign up for free!

But first, here is the best first date advice EVER.

Prior To The Date


  • Guys: Send a reminder text or email the morning of, or the night before the date, to confirm that it’s still on.
  • Guys: When choosing a date location, ask her what area of town is convenient for her. From there, give her 2 options: one on the fancier side and one more casual, and let her pick.
  • Go for drinks over dinner. Dinner is too much of a time and financial commitment for a first date, and there is no way to gracefully exit if you know immediately that there is no connection.


  • Talk for hours on the phone prior to the first date. The best way to assess chemistry is to meet in person, and if you cover everything, you’ll have nothing to talk about on the date.

During The Date


  • Ask more questions than you answer. Of course you both want to get to know each other, but nobody enjoys sharing drinks with someone who nervously babbles about themselves for an hour.
  • Maintain eye contact. It is one of the easiest ways to show you’re interested and listening to what he/she has to say.
  • Keep it light. Ask about passions and hobbies rather than more serious subjects such as religion and politics.
  • Keep it short. The ideal time for a first date is 45 minutes to 1 hour. Short amounts of time leads to mystery, leaving your partner wanting more.
  • Ladies: Offer to split the tab. He will appreciate the gesture and a gentleman will insist on picking up the tab regardless.


  • Keep your phone in reach. Checking your phone can become a nervous habit, and gives off the impression that your mind is elsewhere. Plus, it’s just plain rude.
  • Treat him/her like a stranger. Choose a spot at a bar, rather than at a table, and position your body toward your date. If it’s going well, flirt a little by touching his/her arm or let your legs touch.
  • Bring any baggage with you. Stay away from talking about finances, family issues or exes on the first date.
  • Drink too much. A glass of wine or two might help with nerves, but sloppiness on the first date is never attractive and a sign of immaturity.

After The Date


  • Wait too long to call if you are interested in a second date. There is no “three day rule” when it comes to dating.
  • Cyber stalk immediately after the date. A Facebook friend request after a first date can come off as creepy.

This article was originally published at Guest of a Guest. Reprinted with permission from the author.