Dating again after a long relationship ended? Some do’s and don’ts


When Amelia Pushelberg’s seven-year marriage ended in 2021, she was eager to find love again. “I do want a life partner to share my life and adventures and grow together,” says the 31-year-old, who is based in Ottawa.

But the dating market she’d be re-entering has drastically changed since 2013, when she was last single. Pushelberg had some inkling that being single again would be challenging. “A lot of my girlfriends had talked about the dating apps, not exactly in the best light,” she said.

By July, Pushelberg felt like she was ready to dive back into the dating market. But she was disappointed by the dating apps she joined. “I did (Hinge) for a week and decided it wasn’t for me,” she said. “The effort of having to restart a conversation with so many different people about the same topics felt like a very forced connection.”

Many Canadians, like Pushelberg, have seen their marriage or long-term relationships end during the pandemic. Toronto dating coach Rebecca Cooper Traynor says about 60 per cent of her clients are divorced, compared to 40 per cent in 2019.

“The pandemic made a lot of people look at their situations and their relationships,” she said. “A lot of relationships really broke down during the pandemic.”

Cooper Traynor says that newly single people might feel more lost or stressed since COVID-19. “People coming out of these marriages looking to date again, they are terrified. But it’s almost in a different way where the stresses of the world are also on their shoulders.”

While Pushelberg has shied away from dating apps, Cooper Traynor encourages her clients to embrace them.

“Since the pandemic started, our service went from traditional matchmaking to more of a modern approach where we’re actually helping people find their match on online dating sites,” she explained. “That’s new to us.”

She reassures newly divorced singles that there are many others in their position looking for love online. “When they first approach us, they feel very alone because everything’s changed for them and they don’t know what to do. But when they see a lot of other people in their situation, it makes them feel better.”

Before re-entering the dating scene, Cooper Traynor recommends newly single people “check in” with themselves. “Recognize what you’re looking for in somebody and the kind of relationship you want,” she said.

A common occurrence, she added, is forming their search around their previous relationship. “People are looking for someone exactly opposite of their previous partner,” she explained. “It’s almost in spite, like they want to meet somebody that’s not like them.”

Alternatively, some divorced singles gravitate toward similar personality types, even if they’re incompatible with them. “They might be comfortable with somebody that’s aggressive because their ex was that way, but that doesn’t mean that that’s well-suited for them.” Cooper Traynor helps her clients learn more about their triggers, red flags and “why they might be choosing somebody that’s not healthy for them.”

Figuring out when you’re ready to date again is also something that takes some inward introspection, according to Taranta Lo, a dating coach from Datewrx.

“Why do you want to date? Is it because you don’t want to be alone? Then you might not really be ready,” she said. “ That’s kind of the worst reason because then you might not be making smart decisions and you can get taken advantage of.” Instead, Lo looks for positive signs, like feeling good about life, “having your stuff together” and being in a state of good mental health.

Once you’re ready to hit the dating market, Lo says it’s helpful to be up front about your status as someone who’s separated or newly divorced. It’s something that Pushelberg stated outright in her dating profile. “I’d rather everything was on the table,” said Pushelberg. “If somebody doesn’t feel comfortable dating me because I’ve already been married, then I don’t have to interact with them.”

For people feeling detached from the online nature of dating, as Pushelberg has, or yearning for the “old school” ways of dating, Lo recommends taking online matches to the phone instead. “Back in the day, you talked on the phone to get to know someone. You can see whether there’s a vibe there and if you want to actually go on a date with them. Texting can get frustrating.”

The downsides of looking for love might come as a harsh realization for some folks new to dating after divorce. Cooper Traynor also encourages anyone who is dating again after a long relationship to be realistic about their expectations and anticipate some challenges along the way.

“Dating has its highs and lows,” she said. “Every bad date is leading to ‘the one.’ Don’t get lost in the frustration.”


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