Breakups are rarely just endings — they’re often turning points. Whether someone is healing, thriving, or somewhere in between, past relationships tend to leave a clearer sense of self, boundaries, and what true connection looks like.
For this edition of This is Dating Now, Now Toronto asked locals: What did your last relationship teach you?
From hard lessons to quiet realizations, Torontonians revealed just how much growth can come from heartbreak, and relationship experts shared some words of wisdom with Now Toronto too. “It really taught me that you need to be with somebody who supports you 100 per cent—someone who’s always going to believe in you, always going to be your biggest cheerleader,” Jessica Keffer said.
“And that’s what I have in my current relationship. Luckily, you know, we’re getting married soon, and my last relationship really taught me that—it taught me what to look for.”
According to Laila Kodar, senior matchmaker and director at Select Matchmaking, this kind of post-breakup clarity is common.
“Many realize that love alone isn’t enough,” she said.
“Shared values, emotional safety, and communication styles matter just as much, if not more.”
For Gloria Lemon, who is in her first relationship, the learning process is ongoing.
“I’m learning that other people can be patient with me and just how to show up for people better. Just being there is a lot better than walking away,” she shared.
Nishaana Jeyakumar, a qualifying registered psychotherapist, says this type of emotional reflection often stems from deeper psychological patterns.
“People unconsciously recreate familiar relationship dynamics—even when those patterns are harmful,” she told Now Toronto on Friday.
“Someone who experienced inconsistent caregiving might be drawn to emotionally unavailable partners, mistaking that inconsistency for chemistry. But it’s really the nervous system trying to resolve childhood attachment wounds.”
Michelle Au Yeung shared that her last relationship helped her better manage conflict.
“It taught me how to be more patient and less reactive, and to understand that people react based on their previously conditioned experiences. So, just take that initial reaction with a grain of salt and give people space,” she said.
That kind of emotional regulation is crucial, Jeyakumar adds.
“Most people discover they fall into one of several communication patterns, conflict kind of avoiders, criticism defaulters, or emotional flutters,” she said, referencing the Gottman Institute’s ‘Four Horsemen’ theory.
“So, many people realize they’ve either had rigid boundaries to avoid vulnerability, or overly permeable ones that lead to losing a sense of identity. This learning often comes mostly from grief and mourning, both the relationships and parts of themselves they’ve kind of abandoned.”
Meanwhile, others shared lessons rooted in relationship dynamics that didn’t work.
“I can’t handle a long-distance relationship. Communication’s tough,” Eve Mckenzie said.
“It taught me how to be versatile,” Par Deshmekh said.
“You have to improvise. Every relationship calls for different needs, so you have to be emotionally available and well-suited for your partner’s needs.”
“To be transparent, but at the same time, be aware,” Andrew Bond noted.
Shuti Anish summed it up simply: “NEVER SETTLE!”
After a breakup, some individuals believe they need to be fully healed before dating again.
But according to Kodar, this can be a limiting belief.
“Growth is ongoing,” she said.
“What matters more is being emotionally aware, open and honest about where you’re at. Love requires some level of risk. Protecting your heart too much can also block the connection you’re truly seeking.”
Jeyakumar encourages clients to reflect on their relationship patterns and personal needs before pursuing something new.
“A lot of people tend to go into a relationship and then immediately, or in a few months, they start being co-dependent. That dependency kind of changes as we get out of that honeymoon phase. So, knowing that, going into a relationship, makes a big difference, or understanding that it is going to happen after a certain point is going to help you kind of move around when you’re stuck in that kind of position,” she explained.
Kodar agrees, noting that lessons from previous relationships often result in more intentional dating.
“Clients start prioritizing emotional connection, lifestyle alignment, and how someone makes them feel—rather than just ticking boxes,” she said.
Have a dating experience to share? Email news@nowtoronto.com to be considered for a future edition of This Is Dating Now.
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