Published May 13, 2004 in issue 0319 of The Hook

By MATCHMAKER

The Background

Over-50 dating may be tough, but it also comes with its own set of benefits. Children tend to be a bit older, obviating the need for a budget-busting babysitter. And singles tend to know themselves a bit better, allowing connections to be made-- or missed-- relatively quickly.

Tony, a 50-year-old general contractor, entered the Challenge because he wanted to find a woman who'd be as comfortable tubing on the James as dressing to the nines. A California native with four grown children, Tony said all the right things. "I can find something beautiful in every woman," he promised.

When Deirdre, a 52-year-old horse lover and single mother of two, stepped up for the Challenge, Matchmaker felt certain Tony wouldn't have to look too hard to find something lovely. A kayaking enthusiast with a model's frame, Deirdre offered references and promised she didn't "look like a horse woman."

Tubing? Kayaking? Sounds like a river of fun...

The Date

Deirdre and Tony met for dinner at Al Dente above Escafé on the Downtown Mall.

How did you get ready for the date?

Deirdre: I took my daughter out to eat before. She was dying to find out where I would be having dinner so she could spy on us. Children have a strange fascination with watching a parent in a dating situation.

Tony: I will admit to double-checking my trousers and shirt and my overall appearance.

Were you first or second to arrive?

Deirdre: I was second.

Tony: I arrived 5-10 minutes early. I passed the time speaking with owner/hostess Joia. [Her husband is the chef.] Then I studied the wine list.

Nervous?

Deirdre: No. Dating doesn't usually make me anxious. (Nervous is for testifying under oath before Congress.)

Tony: I felt relaxed but wanted to meet my date for the evening.

What was your first impression?

Deirdre: He was very attractive, actually. Nice friendly smile, tan and healthy with very blue eyes. He was warm and outgoing. He seemed relaxed but energetic.

Tony: My first impression was that this was a classy woman, nice taste in clothing and warm smile.

Deirdre: I think he was wearing a blue shirt and beige pants. Casual and suitably hip but not screamingly "cool." (No comb-over.)

Tony: Deirdre looked great with black mid-calf-length pants, a lime green V-neck with white T under. She carried a cool looking red leather handbag.

What did you order?

Deirdre: He had a glass of wine, and I had a red wine spritzer. A wimpy drink, but other than tequila, alcohol gives me a headache. It wasn't a tequila kind of night.

Tony: The food and presentation were great. Deirdre ordered shellfish, and I had stuffed calamari.

Deirdre: The food was spectacular! I'd rate this as one of the best meals I've had in Charlottesville. A wonderful blend of food and flavors. The plates were beautifully presented without that contrived over-decorated look. I was frightened by his appetizer... an alarming looking stuffed calamari. He assured me it was delicious, but I remained skittish.

Tony: For dessert we decided to share a piece of tiramisu, but Joia brought us two pieces and explained how her husband had just prepared it that day. Towards the end of dinner, Joia introduced her husband, the chef, to us-- a nice touch.

How was the conversation?

Deirdre: The conversation went all over the map. Wrestling with the IRS, real estate in town, moving to Charlottesville, our kids, his ex-wife "Judy," my ex-husband "the Lizard." We both talk a lot, we like the blues, good food, are concerned for the mess this administration is making abroad. I think I might be a little acerbic for him, though.

Tony: We talked about family-- living in different areas--careers-- what brought each of us to Charlottesville, and dating at 50-something

Deirdre: He seems to have a happy relationship with his kids and ex-wife and takes good care of them. I think he's very self sufficient and responsible. He was also polite to the restaurant staff. That sounds trivial, but you can tell a lot about someone by the way they interact with service personnel. I never did find out exactly why he moved all the way out here from California. He swore he wasn't a serial killer.

Tony: Deirdre is quite the horse lady-- I liked the fact we had similar values with regard to children and family.

Any flirting?

Deirdre: No flirting, at least on my part. He was a little touchy-feely, but I think that's a California thing, isn't it?

Tony: There was no flirting, and her body language told me to keep my distance.

So what happened at the end?

Deirdre: I think we lingered over dinner a long time, so he walked me to my car. No torrid stuff to report, sorry.

Tony: Dinner was very leisurely. It was late when we left Al Dente, so I walked Deirdre to her car. She had her seat belt on and hand on the door before I could get her phone number. No good night kiss, no holding hands.

Would you see this person again

Deirdre: Although I'm not looking for a boyfriend right now, I would highly recommend Tony to someone who is in the market. He seems like he'd be entertaining and a fun person to hang around with. Besides being handy around the house, he apparently likes to cook and clean-up! This guy could be a gem!

Tony: I had a good time and would date Deirdre again, but I think she is not all that keen about dating.

On a scale of 1-10, how would you rate the date?

Deirdre: 9

Tony: 7

If you're like Matchmaker, you're wondering what happened to Deirdre-- she has a great time with a guy she calls funny, smart, and attractive-- a 9!-- yet she isn't interested in dating? Hmmmm. This might be one for Unsolved Mysteries...

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