First and Last Date All in One

By Cheryl Lavin

January 6, 2017 4 min read

Today, we hear from Mira. She'd been dating for six years, since her divorce. As so many of us know, dating can be brutal, so she took a yearlong hiatus. When a friend offered to set her up, she decided to get right back on the horse.

She and Alex talked on the phone for two months and exchanged photos. Then, they arranged to meet in person. Unfortunately, Alex lived a five-hour drive away. That ruled out any casual if-we-don't-like-each-other-we-can bail-after-15-minutes coffee dates. A dinner date was also pretty much out of the question. What would happen to Alex at the end of dinner? Would he have to get in his car and drive five hours back home?

"You cannot just end the day when someone has made that much effort," says Mira. That's what the weekend was named for. So a weekend was arranged.

Alex arrived on Friday night, checked into the hotel and called Mira. She was out with friends having drinks and invited him to join them. He said he was "a little tired" from the drive. She offered to come by the hotel and say hello. When she arrived, he appeared freshly showered "with some weird wet hair action going on." The strong smell of Old Spice wafted off him.

"I was not too impressed," she said.

On Saturday morning, Mira invited Alex to her house for breakfast. He arrived wearing mom jeans. She cooked him pancakes.

"It was a nice, simple breakfast, but he did not say thank you," she said.

The next order of the day was a trip to downtown Chicago and a boat cruise on the river. They took the train into town. Mira suggested they take a cab to the boat, so they could be sure to get a good seat. Alex insisted they walk. Walk they did. Actually, they half-walked, half-ran.

She said: "At one point, we were running and Alex was laughing. I asked, 'Why are you laughing?' He said, 'I'm laughing with you.' I said, 'I'm not laughing.'"

They got to the dock three minutes before the boat was scheduled to leave. All the seats were taken, so they have to stand for the 90-minute tour.

She added: "If we had taken a cab, we would have had a seat on the top deck. He never even asked me whether I wanted a drink."

After the tour, they headed over to Navy Pier. Mira said she was thirsty and walked over to the drink stand. She pulled out her wallet. Alex made a show of offering to pay but let Mira do it. She ordered a beer; he had lemonade.

They headed back to the suburbs for pizza. It came down to one piece of pizza. Alex wrapped it up and said he'd eat it for breakfast.

"For some reason, he found it appropriate to burp with the ease that one should only feel after dating for years," she said.

After the pizza, they went back to Mira's home. She said: "He had that are-you-going-to-invite-me-in look. I told him I was tired and that I'd talk to him the next day."

Alex spent Sunday doing who knows what and finally called Mira Sunday night. She didn't answer the phone.

"Can you blame me?" she asked.

Next, Mira's friend Chuck tells Alex what he did wrong.

Send your tale, along with your relationship questions and problems to [email protected] And check out my new e-book, "Dear Cheryl: Advice from Tales from the Front."

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