The dater
Keysha Freshh has released 11 albums and multiple singles, and collaborated with artists like Maestro Fresh Wes and Solitair. In 2023, she was nominated for Children’s Album of the Year at the Junos. She was part of the hip-hop supergroup The Sorority. Her new album “Pretty Boys Break My Heart” comes out August 16.
The dates
I’ve been single for about two-and-a-half years. I like being single because I don’t have any emotional obligations to another person right now. It allows me the opportunity to enjoy myself and my own space and time. I dislike being single sometimes, though, as I just want to cuddle and watch a movie with the person I love, and I don’t invite any and everyone into my space like that.
I’ve actually never used a dating app, ever. They terrify me. I don’t love dating here. When I’m out and about, it’s usually something to do with music, and I have a rule of not dating anyone in my industry. Everyone knows each other: for such a big city, it’s so small!
My worst date was with this guy who’d been asking me out for eight months. I finally obliged, and when we got to the restaurant, he ordered steak. I don’t eat red meat, so my meals are usually within a reasonable price range. He ordered dessert and drinks, and insisted I did, too. Next thing you know, the bill comes, and his card is declined super-loud: I mean, the machine was out to embarrass the guy. He then opens his banking app, and says “Oh, (my) deposit didn’t hit yet, can you cover it? I’ll pay you back.” I couldn’t tell you to this day if (his) deposit hit because I never spoke to the lad again.
I’ve had many great dates and experiences, though, too. My ex paid attention to details. He knows I love seafood, so whenever we went away, he would make sure we tried a new seafood spot. We did zip-lining in Niagara. I love sports, so a nice live game and a nice meal after is a good vibe for me. As for my go-to Toronto date spot, I love West Indian eats, so I like going to Windies Restaurant. That’s my spot.
The inspiration to name my new album “Pretty Boys Break My Heart” came from a few different experiences, actually. Not just romantic ones but also losing my high school sweetheart in a motorcycle accident. My best friend passing: that, too, broke my heart. And then, of course, breakups and classic heartbreak. Pretty boys who know they’re handsome, are the worst! Hook, line, sink.
One of the hardest parts about dating as a public figure is people gossiping. I’m actually a very private person when it comes to my love life. And so not having my significant other on red carpets or at events can cause tension in our relationship. I’m not trying to hide them from the world; I’m trying to hide this world from them. There’s a lot of misconceptions that we as artists are too busy to balance work and relationships. We make time for the things we care about and love. I was on tour but still made sure that I checked in regularly and didn’t miss a beat in my last relationship.
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