Help! I’m going on a first date. What should I do?

First dates can be intimidating, especially if you’ve never met, or have had minimal face-to-face contact. Relax, take a deep breath and follow some of these tips to help you through.

Take the stress out of the “first date” with humor, practical thinking and, above all, a positive attitude. Have no expectations, and welcome the contact even if he or she only becomes a new friend!

Senior Singles, It’s Your Attitude That Counts!

Do an attitude check. Don’t fantasize or romanticize before the first date. I was super-guilty of this one in my younger years. I would get so excited that I’d already planned the wedding and the honeymoon even before a first date.

Luckily, with age comes more grounded thinking. It’s also important to check if you’re ready for dating after a divorce or a loss. The new person deserves a fresh shot and unbiased opinions with no comparisons – positive or negative – to your ex- or late partner.

Make Sure that You Don’t

  • Share too many medical, financial and family facts.
  • Boast your credentials.
  • Talk too much about the ex- or the departed.
  • Be judgmental.
  • Drink too much.
  • Have sex on a first date (unless you have weeks to live).

“You Look Just Like My Dead Ex-Wife”

On our very first date, Marvin told me that I looked just like his dead ex-wife. If that wasn’t enough of a turnoff, he added that he keeps her ashes on his bedside table.

On my friend Debbie’s first date, she told Henny Youngman one-liners all night. So, it’s good advice to try your jokes out on other people before you try them out on a first date, and limit them.

My colleague Allan went on a date with a woman who described her mood swings as she downed pills during dinner. Another friend, Warren, listened sympathetically about his date’s financial problems for several hours. Then he ran for the hills.

As mature daters, we carry a lot of baggage. Don’t unload it on the first date. Keep the conversation light yet interesting. It’s the perfect opportunity to explore common interests with your date.

The Do’s for Senior Singles

  • Dress comfortably, smart and appropriate for the venue.
  • Pick a public venue for a drink or coffee.
  • Look for red flags in behavior, manners and back-story.
  • Be charming and relaxed.
  • Exude confidence.
  • Put a post-it with the contact info of the person you’re meeting and the venue on your laptop or desktop screen.

Use Common Sense

You’re all smart cookies and will navigate the first date well when you have a positive attitude, a doze of rational thinking and adjust your expectations. Happy dating!

For more “Do’s and Don’ts,” check out Sylvia’s boomer dating guide and workbook in my novella “Suddenly Single Sylvia.” The guide is based on a team of dating and singles experts as well my own personal experience of dating after divorce and loss.

Have you been on a first date after losing your partner or going through a divorce? What was it like for you? Could you have done things differently? What dating advice can you offer the senior singles in our community? Share your first date experiences below as well as pitfalls to avoid.

Angela PageAngela Page is a writer and producer. Her recent release, “Suddenly Single Sylvia,” is a novella and dating guide. In 2015, her award-winning comic romance, “Matched in Heaven,” and short comedy, “Unplugging Aunt Vera,” were released. Angela divides her time between Boca Raton and Los Angeles.

Let's Have a Conversation!