Second chance dating may be a favorite in the books, but is it a good idea in real life?
This is one of the interesting topics discussed by book promoter Morgan Book, author Joss Richard and Bookends host Mattea Roach at an event at Hamilton Public Library earlier this month.
The book supports Richard’s first book It’s Different This Time to Canada is Reading 2026, show there five Canadian celebrities each choose one book they think the whole country should read. They debate their choice over the course of four days, choosing to eliminate one person each day. The last book standing is the winner.
This year’s edition will be from April 13 to 16.
It’s Different This Time it’s a second chance dating with actress June Wood.
When June’s TV show is canceled, she has no reason not to follow up on a mysterious email inviting her to return to the New York City brownstone where she lived before moving to Los Angeles. It is the house that was left to her and her former roommate, Adam, by the original owner.
The attractive property will soon be theirs – they have to stay together for four weeks while they complete the paperwork. One catch: June and Adam haven’t spoken in five years and they’ve left some pretty cool stuff behind.
The more time they spend together, the more they are reminded of what they had, and how painful it was to let go.
For special edition in place of BookendsRoach, Richard and Book dish about exes, the magic of New York City and finding yourself in your 20s and 30s.
WATCH | Joss Richard and Morgann Book on Bookends in Hamilton:
Mattea Roach: Here’s a question from the audience – what is your favorite romantic trope and why?
Morgann’s book: Damn there are so many. I was going to say recently though, I really love friends to lovers and I never thought I’d say that, but I feel like friends to lovers are the new enemies to lovers.
Enemies to lovers are no longer believed. I get that there can be competitors, but no one will believe that two people want to break up in a romcom. I find friends in the fans who are very nice and reliable now.
I like autobiographies It’s Different This Time. I like autobiographies The people we meet on vacation, as those are very strong competitions for friends to lovers.
Joss Richard: I would say a second chance at love, naturally, because It’s Different This Time it’s a second chance to fall in love. I would love to read a second chance at love again. It’s funny, because I wouldn’t recommend a second chance at dating in real life. Don’t get back together with your ex. Don’t do it. There is a reason why you are divorced.
But it’s fun to read and it’s fun when it’s not you.
The two former roommates inherited a house in New York City where they lived together. Joss, for anyone who hasn’t read the book, can you lay the groundwork? How did you come up with this idea?
JR: I have always admired my energetic roommate. My favorite TV show growing up is a very old TV show from the 70’s, 80’s called Three’s Company. I loved watching these friends live together.
I love the show Friendsi like The New Girl. I love friends who stay together in their 20s and become your family, mostly.
I liked the story of two people, especially my roommates, who are very much in love, but they didn’t love each other. It also follows the theme of the one who got away and would you do things differently if you had a second chance?
So I feel like all these questions I had about relationships and power, I put them in this book and that’s how this idea came to my head.
Joss, what is your relationship with New York and romance?
JR: I grew up on Nora Ephron, so I always loved New York, especially New York in the fall. I feel like it’s the most romantic place and time of year.
Living in Toronto, I feel like every long weekend my friends and I would get on a big bus and go to New York. It was 20 dollars and we would be on a big bus for nine hours.
I fell in love with New York because I didn’t live there. So I feel like every time I go it’s always this fun, fun experience. When I wrote this, I was thinking, “Okay, where am I going to do this?” New York was a no-brainer because I find it fun and romantic.

June is our opponent. I am an actor from Toronto. He is bright, funny, passionate. She’s also in her 20s and now in her 30s, dealing with some insecurities. Morgan, I want to ask you about your thoughts on June as a player. How do you relate to him as a narrator and how do you feel about his journey?
MB: I loved her as the main female character from the beginning. I thought he was very friendly. I really liked that he didn’t know everything in his 20s or 30s. He was always fighting this battle of what I wanted to do against what should What do I do?
Although I couldn’t relate to the parents’ side of it – my parents were very supportive while June was really fighting with her mother not showing up – I think the constant battle of, “what opportunity am I following?” Even at the end, he faces that again. I really liked that.
I think no matter what stage I read this book in, even 10 years from now, I think I would relate to the feeling of, “I don’t know what I’m doing with my life.” And that’s okay.
Do you see yourself on that journey at all?
MB: It’s different, especially because I don’t know anything about theater, but I think I saw myself in June with her desire for something – it was theater for her and books for me.
I looked into law school and it just didn’t make sense. Just like June was out of touch in the movie and TV world. As if something is missing. I loved going to McMaster. I loved studying political science, but something was missing.
I think that’s where I saw the connection, thinking I could make a life out of my passion for books like June did for theatre.
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