From dating disasters to lasting love

“He insults his ex”; “She never shuts up”; “The date went terribly”; “We’re just not meant to be.” Though sometimes reservations about someone are well founded, in other cases, a negative first impression or disastrous date can lead to a classic love story.

In a case of legitimate reservations, Tanya Jacobs* ensured that her first-date disaster never technically transpired. “After my divorce, the owner of a small supermarket saw that I’d lost a substantial amount of weight and thought he’d be doing me a great kindness by making a shidduch between me and the manager of his store,” she recalls. “He didn’t know my background at all, he simply thought it was a phenomenal idea because the store manager and I were both divorced.”

When her fellow divorcee called Jacobs, he told her that they had a lot in common because, he assumed, they both hated their exes. “He proceeded to tell me about how he fought not to pay maintenance for his child,” she recalls. “He then asked if I could fetch him for the date as he had sold his car when he was still paying maintenance and now rode a bicycle and felt that riding in tandem wouldn’t be appropriate.” Jacobs summarily told him that she didn’t feel ready to start dating yet, and cancelled.

However, returning to the supermarket became increasingly challenging. “Every time I went there, he would stalk me in the aisles,” she says. “When I did eventually start dating someone, I was excited, not because I was thrilled about the guy, but because I asked him to come with me to the store and to give me the biggest smooch ever.” Needless to say, the aisle stalker ceased his activities.

In spite of some missteps along the way, Hilary and Kevin Kaplan’s story had a far better outcome. Introduced by a mutual friend, they first met at a coffee shop. “While we were getting to know each other, I mentioned that I really liked ice skating, and Kevin said he had done it a few times as a teenager,” Hilary recalls. “He suggested that we go together.”

Little did they know that this would be the setting of an unmitigated third-date disaster. “I drove us there, and we put on our skates and stepped onto the ice,” she recalls. “Kevin was holding onto the side, feeling unsteady. Within five minutes, before we had even done a full lap around the rink, he lost his balance and fell onto the ice. He had dislocated his knee, and I could see the bone pushing out the side of his leg. I screamed for a medic to help us, and he was carried off.”

Hilary followed the ambulance to the hospital, helped Kevin fill in his medical forms, and kept him company while the pain medication kicked in. What could have been its demise, turned into a key moment in their relationship.

“That was the night I discovered what his middle name was, his birthday, and the fact that he doesn’t have any allergies,” Hilary says. “Throughout the night, Kevin was in pain, but didn’t lose his positive attitude as we chatted while waiting for the orthopaedic specialist to come and pop his knee into place.”

The date ended around midnight, when Hilary met Kevin’s parents, who had come to drive him home and pick up his car which he’d left outside her house. “It wasn’t the first impression I was hoping to make,” she says. Yet, as a result of the experience, she learnt how brave and kind Kevin was. “A year later, we got married and 14 years later, we’re still happily married. However, I’ve never taken him ice skating again.”

The first time Dani Levitan met her husband, Greg, she was about to move to Australia. “Friends of mine wanted to set me up with him, and I didn’t want anything to stop me from moving,” she recalls. Yet she agreed to meet him, with their first encounter taking place on the dance floor at her best friend’s wedding. “It was pretty awkward because it was quite contrived,” Dani recalls. “We went on a couple of dates though, but I knew he wasn’t for me.”

Dani says that though the dates weren’t bad, she thought Greg was a little nerdy for her. “Instead of the mensch, I wanted the bad boy. Regardless, nothing was going to stop me from moving to Australia.” Though Greg really liked Dani, his calls to her to wish her luck on the day she moved went unanswered. “I was so horrible about it,” Dani recalls. “To this day, he still mocks me.”

Dani hated Australia, and ultimately returned to South Africa. Soon afterwards, she ran into Greg at a Rosh Hashanah lunch at mutual friends. “My mother asked who he was, and I said, ‘He’s not for me.’ I thought she just wanted to hook me up with anyone to ensure that I didn’t go overseas again. Greg and I chatted briefly, but it was a bit awkward.”

Months later, debating whether or not to delete Dani as a Facebook friend, Greg decided to message her instead. After two weeks of mutual messaging, he asked her out. Though she still felt that Greg wasn’t the one, Dani thought, “Why not, nothing ventured, nothing gained.”

Their second first date – almost two years after the first one – turned out to be amazing. “From there, it just evolved,” she says. “We started speaking every day, and my feelings completely changed about him. If I hadn’t gone, I wouldn’t be in the position I am today, married with two beautiful children. It’s always worth giving somebody a chance.” She says it was she who needed to change, not Greg. “I always say to him, had we dated properly the first time around, I probably would have messed it up and we wouldn’t be together today because I wasn’t in the right head space.”

Undeniably, there are multiple factors to the process of finding lasting love. Shadchan Cindy Silberg says she always suggests that her clients commit to at least three dates before ending things unless they see a bad side of someone or feel unsafe. “In my eight years of experience, I’ve seen that most first dates don’t go as well as the couple were hoping. This is probably due to them being nervous and not knowing the person.

“When people go on at least two or three dates before making a decision about whether to continue or not, they have a lot more insight about their choice,” she says. “I’ve had many couples who were about to stop seeing each other because of a bad first date and I convinced them to go on another one. Often these dates have turned into beautiful marriages.”

*Name has been changed.