What if the hardest thing about dating was just deciding to do it?

Simone Biles, the most decorated gymnast in history, is poised to win yet another gold at the Summer Olympics in Paris. Has it always been easy? Hardly. At age 3, she and her siblings were placed in foster care because their drug addicted mother couldn’t care for them. Raised by her grandparents who provided Biles with both support and encouragement, Biles still had to come to terms with the challenging and unique circumstances of her life.

From the relentless push to perfect her craft beginning at age 6, to the numerous sacrifices she made to live the life of a prodigy athlete, to the outsized courage she demonstrated in speaking out about sexual abuse, Biles has become a leader and a role model.  In each case, she knew she’d regret it if she never risked and took a chance.  

Think of Biles’ success as a parallel to our journeys of dating in mid-life.  Just as she has throughout her career, we too must decide if stepping into the unknown could be worth it.

After the end of a marriage or a relationship, or any other change in circumstances which breaks apart the vision we have for our lives, we can decide to stay as we are. (After all, the mental and physical energy required to date again is daunting.) OR, we can cast off that point of view, and venture into a new world that will most certainly change our narrative.

The four biggest hurdles of thinking about dating:

What are the universal fears that singles express about dating in midlife?

For me, it had been 30 years since I had dated in my 20’s. I knew how rusty I was when I started dating again after 24 years of marriage. What helped me most was analyzing each of my fears, one at a time. It didn’t take long before I realized my worries weren’t as much about dating in general, as they were about different parts of the date:

1) Getting ready – what in the world do I wear?

2) Arriving – how do I make an entrance when all I feel is nervous?

3) Conversing – what do I talk about on a date?

4) Ending it well – will there be a second date if I liked this one?

 Once I figured out how to overcome those concerns, dating became so much less stressful. While it was true that every date wasn’t perfect, I can honestly say they went as well as they did because I always subscribed to the following seven rules.

Here’s how to date with ease:

1. Get into your “people” mode and out of your “own head” mode. As you get ready, start thinking more about the person you are going to meet and what you are curious about, and less about your concern that you might be somehow deficient.  

2. Decide what you are going to “bring”. Maybe you arrive with a small gift. (I have been known to give Starbucks cards, $2 bills, or an icebreaker riddle in an envelope.) Or you’re arriving with an interesting bit of news. Or you commit to being a good conversationalist. Think about how you won’t show up empty handed.  

3. Wear what you feel great in. No matter what outfit you choose, the cut, the color, and the style should boost your confidence. Then try it on first with all the accessories.  

4. Walk into your meeting place with a friendly demeanor and a smile. Show that you are genuinely happy to be there, whether for 15 minutes or 4 hours. Make eye contact, offer your hand, and demonstrate open body language. Be easy to be with.  

5. Have a great welcoming line. Whatever you first say, make it genuinely reflect who you are. Show your personality by the way you deliver your opening words. Demonstrate energy. Extend yourself by being warm and gracious.  

6. Edit your story. Before you begin the conversation, know what three topics you’d like to talk about. Then decide how they work as stories and how you’ll tell them. They don’t need to be lengthy, just interesting. If it helps, try them out on a friend.  

7. Say thank you! Whether the date was fabulous or forgettable, whether you paid or they did, whether you want to see them again or not, leave a good impression by expressing gratitude. If the situation warrants, follow it with a text the next day.

Here’s to your dating success! Let me know how it goes at Kate@KateSomerset.com.