Magazine

Dinner With Cupid

Blind date: ‘When she told me she might get “Hamilton” tickets next year, I was smitten’

He blew his chance with Oprah, will he rebound with Cupid?

Wallace Tilford and Helen Witherspoon.

WALLACE TILFORD: 63 / community relations

Who plays him in the movie: Denzel, of course

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Notable qualities: He once made D.L. Hughley laugh so hard he spit his drink out.

HELEN WITHERSPOON: 64 / manager

Notable qualities: She is writing a memoir.

What makes her a catch She’s in great shape and good health.

8 P.M. TEN TABLES, JAMAICA PLAIN

PRE-DATE PRIMPING

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Wallace I wondered if I could find an interesting baby boomer from Boston.

Helen I thought, why not involve older people? We are still in the game.

Wallace I did my hair and spritzed on Bleu de Chanel.

Helen I spent hours being pampered at the hair salon. My stylist was so excited she added a special touch at no charge.

Wallace I was early so I was able to snag a primo table. Helen arrived exactly on time. She was very attractive. The staff complimented us on our attire. We did look good. Helen had a very nice hairdo.

Helen He was tall, nice whitish hair. It was obvious he had taken time to dress, which I appreciated.

MISSED OPPORTUNITY

Wallace We talked about our grandkids.

Helen He has a love for antiques, museums, traveling. We both have grandchildren that we adore. I kept the conversation general, based on advice from my hairdresser.

Wallace We shared concert experiences. Luther Vandross and Earth, Wind & Fire!

Helen I suggested we share the mussels, but mussels being his favorite, he said no with a smile. He still ended up giving me a few. We ordered steak. Dinner was superb.

Wallace The staff gave us complimentary champagne and wine! When Helen inhaled the dessert tart with glee, I had to laugh.

Helen We found it easy to crack jokes.

Wallace I told Helen about meeting Oprah at a party when we were both 18. She laughed and said, “If you only knew!”

Helen He asked [her] “What kind of name is Oprah?” I teased him that he could have been “Stedman.”

Wallace When she told me she might get Hamilton tickets next year, I was smitten.

Helen He seems maybe too easygoing. I do like a little of an edge. Then, again, he didn’t want to share his mussels.

Wallace We talked about going to breakfast together soon because she has never been to Mike’s Diner. Wha!!?

Helen He grabbed the check. He also left a big tip! I was impressed that he took the lead, maybe he does have an edge.

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LASTING IMPRESSION

Wallace We walked in the rain to our cars and exchanged numbers.

Helen He opened his umbrella and held it over me until I got inside my car.

SECOND DATE?

Wallace We will do a breakfast soon.

Helen I think there is enough smoke to at least see if there’s a flame.

POST-MORTEM

Wallace / A

Helen / B+

Go on a blind date. We’ll pick up the tab. Fill out an application at bostonglobe.com/cupid. Follow us on Twitter @dinnerwithcupid.
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