10 Tips for Successful Dating Over 40

You’ve been single for a while. You would like to have a special man in your life. But how?

Women reentering the dating scene after a long absence need to first examine if they are ready to date again. After all, not only is there the possibility of being swept off your feet by a romantic, loving man, there’s the chance of being swept over the cliff of heartbreak. Here are some tips on how to ensure you enjoy your adventure of dating after 50, not dread the next coffee date.

Long-Distance Dating Pros and Cons

Some people set no distance requirements on potential suitors. One Adventures in Delicious Dating After 40 reader shared she was romanced by a guy half way around the world for over two years! (They never met and he went poof one day.)

Other people have ridiculously short distance requirements. Some men list 10 miles as their dating radius in their dating profiles. Unless you live in New York City, I think it this is too small. An hour’s drive seems reasonable to me.

Throughout my post-divorce dating, I was always clear I didn’t want a long-distance relationship. Even thinking that, I’ve been entranced enough with four of the 112 men to explore dating them. With three of the four, I spent hours on the phone with them, often talking every day for up to several months before meeting. Two I never saw after one date, and one I saw 3 times before he went poof.

Then I found myself in a 600-mile relationship. Why? Because he is a great, loving, smart, romantic, thoughtful guy. The distance has its pros and cons. Here’s what I’ve found so far:

When your ex dies

My ex learned he had cancer 2 years ago. Since we didn’t keep in touch, I learned of it a year ago. He did semi-weekly podcasts for a few dozen friends to update them on his health. I listened to the previous 100 podcasts before reaching out via email.

He said he was thrilled to hear from me and was stunned that I would listen to all 100 previous podcasts. I’d asked if now we could be friends and he said he’d like nothing better. We exchanged a few emails and he said he’d like to talk about the end of our marriage as he was sure I had some questions — which I did. I asked for some good times to call since he was so overwhelmed with treatment appointments and recovery. However, he never closed the loop to set up a call, so I decided I’d make the 600 mile trip to visit him and have that discussion face to face. A few months ago, his doctors had given him 18 to 24 months, so there was plenty of time.

Opening the kimono

kimonoWe’d been talking for a few weeks before meeting. I’m not fond of trying to kindle a relationship with someone living 1000 miles away, but he had certain rare attributes I’ve been looking for in a partner, but unable to find locally.

If having sex meant you were married

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Chupah

I attended a lovely Jewish wedding last weekend. The bride was resplendent and the groom handsome as they stood under the  chupah in front of the rabbi (the bride’s father) and the cantor (her god-father). Outside at sunset, the family and friends stood encircling the couple on the grass. The cantor’s sweet singing, including a song he wrote for the bride, soared in the crisp evening air. Candle luminaria lit the lawn on which we all stood, and a lone guitarist strummed entrance and exit music.

I’d arrived early, and my friend (the bride’s mother), showed me and another couple the quaint sleeping rooms in the inn where the ceremony and celebration were held. In showing me the bridal suite, she mentioned that in traditional or Biblical Jewish tradition, when a couple has sex they are then considered married.

Wow!

An awkward situation

In midlife dating, we sometimes encounter situations that are just too awkward to have a ready-made answer. I remember one from early in my dating re-entry. I wish I could forget it. I’m not sure I would have an easy answer if it happened again.

Being “all that”

In high school, if a girl is described as thinking she’s “all that” she’s considered arrogant, conceited, stuck up, snobbish. She thinks she’s God’s gift to the world. She’s too good for mere mortals.

Yet, when a young man describes a young woman as “all that” it’s a high compliment. He’s saying she’s sexy, attractive, desirable.

“Women are work!”

He said this with exasperation. He was weary from his last relationship being more effort than he would have liked. He thought it should be easier.

I told him most relationships were are least some work. They could be easy breezy, but there was some “work” involved — one of you had to initiate contact, you had to be willing to work through any hiccups. This could be considered work by some. And when romance is involved, expectations quickly escalate.