In her new book, 50 Worst Dates, Jane Laboucane shares some of her dating catastrophes that will have readers laughing, cringing and sympathizing on the deepest level. Whether you’re single, in a relationship or anywhere in between, 50 Worst Dates is guaranteed to entertain and resonate with anyone who has ever braved the world of online dating, blind setups and awkward encounters in search of love. We chatted with Jane to learn more. —Noa Nichol
Hi Jane! Please tell us a bit about yourself to start.
I’m a Cree Metis woman from a small community in Treaty 8 territory and I’ve been writing in various forms—magazines, peer-reviewed medical journals, short stories, etc.—for several years. I’m in my mid-thirties and I’ve been looking for a long-term partner for the last decade. Unfortunately, how attracted I am to a man seems to be proportionally related to the number of red flags he exhibits. Which, while disastrous for my love life, usually provides entertainment for others. When I see my friends, one of the first things that usually ask me is “have you been on any bad dates lately?”. Nine times out of ten, I have a story that makes them laugh. Dating can feel a bit disheartening at times so being able to entertain others with my stories really puts a positive on the exhausting and, what sometimes feels like, fruitless pursuit of finding a partner. My love life is a disaster, but if it can make someone laugh, then I’m happy.
Congrats on your debut book 50 Worst Dates! What’s it about?
50 Worst Dates chronicles the litany of bad and bizarre dates that I have gone on over the past 10 years in the form of short stories. Half of the book is comprised of bad dates I went on with my long-term ex-boyfriend, Babycakes. He’s a prominent financier and our relationship was a dumpster-fire that provided endless hours of entertainment for my friends and family. The other half of the book’s dates cover everything from one-offs to partnerships that lasted several months. The one thing that they all have in common is that they are some form of terrible—from awkward and embarrassing to jaw-droppingly outrageous.
Of the 50 included in the book, what would you say the absolute worst was?
I think it’s probably a toss-up between the man who tried to rope me into a foursome on a second date—I was too naïve to understand what was going on at the time, I just thought it was a bizarre evening until I told my friends about it the next day. Everything clicked once they clued me in—and the trip to Las Vegas that Babycakes and I went on in a bid to save our relationship. When your partner is the personification of hedonism and you’re throwing the relationship-equivalent of a Hail Mary pass on the final play, Las Vegas is probably the last place that you want to go.
Any advice for other daters, either to avoid disastrous dates or deal with them?
Given the mess that is my love life, I may not be the ideal person to answer this question, but my best advice is to go into a date with no expectations, ask lots of questions, and try and be yourself. And if you find yourself on a date that starts to go horribly wrong? Chalk it up to experience and just think about the story that you will be able to tell your friends. Some people make excuses and leave shortly after they feel things are starting to go south, but I usually opt to ride it out and see just how bad things will get. In for a penny, in for a pound type of thing. Unless, of course, there is any kind of safety concern or really unacceptable behaviour on my date’s part. I would also encourage people to branch out from online dating. I attribute most of the bad dates in my book to Bumble, but that may just be due to my penchant for choosing poorly. There are a myriad of other ways to meet a potential partner—through friends, joining clubs, checking out a new fitness class—so don’t limit yourself to the world of online dating apps. Not that a different method of meeting someone will necessarily save you from going on a disastrous date.
What happens at the end? Is there a happily ever after here, or … ?
Happily ever after? If only life was like the movies. I have the com, but not the rom. I’ve given up on online dating and I’ve been ensconced in a “situationship” for the past two years (he also features in the book). Who knows what the future will hold, but I’m hoping that, ten years from now, I won’t have enough material for 50 Worst Dates part two. Pray for me.
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