5 Pro Tips for Navigating Your First Date

Wendy Newman is a professional dating, relationship, and sex educator. She has led hundreds of workshops for thousands of people in the US and Canada as well as coached private clients. On the personal side, Wendy is a compassionate fellow dater who navigated her way through 121 first dates before she met her life partner. They live together in San Francisco.

Wendy Newman, 121 First Dates, online dating, romanceRaise your hand if you love the thrill and excitement that comes with the adventure of online dating. Come on, raise ’em up high… really? That’s it? Yeah, I thought so.

While most of us don’t exactly enjoy the process, we’re still willing to get out there and hack and slash our way through the dating jungle to hopefully find, at the edge of all that cleared brush, love.

Now that you’re all rested and relaxed from the holidays, it’s time to take advantage of that percolating excitement that builds with the start of a new year. Shake the pecan pie crumbs off your onesie, pull up your online profile (or craft one from scratch), add that super-cute holiday selfie, and hit the “activate” button. Ready?

121 First Dates

121 First Dates

by Wendy Newman

  • Get 121 First Dates
  • Get 121 First Dates
  • Get 121 First Dates
  • Get 121 First Dates
  • Get 121 First Dates

Here are five simple steps to a first date (for the pros and the newbies alike).

• Obtain a date
• Show up for the date
• Present yourself as yourself
• Enjoy getting to know a stranger
• Kindly part ways

Let’s take a look at each step to see how we can make your date go from so-so to good to great!

1. Obtain a date. Obvious, right? Sure, but let’s dig a little deeper. Be prepared to put some effort into it. Don’t just craft a stellar profile with charming photos and witty summaries and then sit back and hope they find you. This is a common mistake that can burn you out on dating before you give it much of a chance at all.

Sift, sort, and select people who are interesting to you. Reach out to them to check their level of interest (yes, you absolutely can make the first move). Drop them a quick line to let them know that out of the sea of millions of daters on this site, A) you exist, and B) they have piqued your interest. Give them a virtual nudge.

Making the first move doesn’t mean you’ll lose power, or seem desperate, or make you any less attractive—quite the opposite, actually. You’re showing interest, initiative, and confidence by lobbing the ball squarely into their court.

2. Show up for the date. Want to make a good first impression? Be on time. Men, be five minutes early. Women, be on time. And if either of you are running late, communicate. We’re living in the information age, people! This is what texting is all about.

3. Present yourself as yourself. “Well duh, of course,” you might say, but this is often harder than you think. If you’re hot for the person sitting across from you, your instincts will do anything and everything they can to present you as whomever they think your date wants you to be—being your authentic self is probably the last thing that will occur to you. Practice presenting yourself as yourself, and dating will go much better for you.

4. Enjoy getting to know a stranger. Given that they’re not your partner (yet) but a total stranger, it’s best to ask them getting-to-know-you questions first. Instead of “What happened to end your last relationship?” or “Tell me all about your management job,” try “What do you love about your life?” or “What’s coming up in your near future that you’re really looking forward to?” or “Who’s your underdog, and why?” These get-to-know-you questions are also feel-good questions, so even if your date is ultimately not your person, the two of you will have an uplifting time together. Dating’s supposed to be fun, after all.

5. Kindly part ways. Again: duh, right? But wait a minute. I didn’t say “nicely part ways,” which is a whole different deal. As my best friend always says, “There’s a big difference between nice and kind.” Nice is when you say, “Um…yeah, sure, call me!” and what you really mean is, “You can try to reach me, but I’m just going to dodge your call with the help of my good friend, caller ID.” If you two are not a fit, and your date asks you out again, opt instead for kindness and say, “Thank you so much for asking, but I don’t see a fit here. I had a great time with you today. Good luck out there.” This may seem blunt, but wouldn’t you want to know up front instead of being led down the proverbial garden path by your date? It goes both ways.

So go forth, daters. Be smart, be kind, and have fun. I’ll see you out there in the world. I’ll look for you at your table for two at the wine bar, the café, or the restaurant. I’ll spot you out there on your first dates, and I’ll be rooting for you the whole way.

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