Posted inDating after 40

The Tryst

He is smart, funny, charming, good looking, worldly, educated, successful, a sharp dresser, good listener and conversationalist. He tells you what you long to hear. He is vulnerable with you and you with him. His kisses and caresses make you feel what you haven’t felt in a long, long time. He tells you how sexy and adorable you are, and how much he misses being with you.

You met through business, not online, so you know he’s not a player.

Yet there are things about him that on paper would be deal breakers.

Posted inDating after 40

Keeping it 100

The phrase “keeping it 100” comes from “keeping it 100% real,” meaning being 100% honest. It’s shorthand for no BS, don’t tell me what you think I want to hear, tell me the unvarnished truth. Don’t hold back.

I decided to try this with a man while we were exploring going from pals to more. His life is complicated right now, uncoupling from a long-term relationship. I wanted to understand his emotional state, goals and desires. I needed to determine if it made sense to become closer during this challenging time, or whether it would be best for all if we stayed pals and revisited becoming romantic after he was fully unencumbered.

Posted inDating after 40

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.

Posted inDating after 40

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:

Posted inDating after 40

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.

Posted inDating after 40

How much mind space does he take?

When I’m smitten, or even in the beginning of a budding relationship, I think about the guy a lot.

“I wonder how his day is going. Should I text him?
“I should ask if he wants to come over for dinner Friday.”
“I need to ask him why his marriage broke up.”
“I think I’ll ask him to accompany to the party next weekend.”

This sort of incessant chatter fills my idle thoughts. I rarely have time to think of my other interests.

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Right man; wrong continent

He was not classically good looking. He had a pronounced nose and craggy face etched from decades of intense work. But his entrancing blue eyes made everything else fade away.

He stood straight so his fit 57-year-old body seemed decades younger. And when he looked at you, it felt like he really saw you. He listened and asked intelligent relevant questions. The combination was sexy — my married gal pals felt it too. He was divorced.

We met speaking at a conference in Singapore. We spent all our downtime together the next 3 days. I invited him to a small dinner party with some of my pals. He got along with them beautifully, balancing listening to their stories, asking questions and sharing his own experiences.

But alas, it was not to be.

Posted inDating after 40

The woo dance

Wooing can be exhilarating, fun, and exciting. It’s nice to be the recipient of a man’s attention and affection. It’s especially nice when he’s good at it, but not so good it seems practiced.

I’ve been the recipient of good woos and not so good ones. The latter wooers seem clumsy, perhaps out of nervousness or lack of confidence. The former seem relaxed; the wooing feels natural, comfortable and sincere. But of course, that could also come from frequent wooing.