Catching the Big One

“Deceiving others. That is what the world calls a romance.”   — Oscar Wilde

When I heard a woman who lives in my neighborhood had written a chick lit tale that takes place in Chicago, I had to read her book. It’s not often guilty pleasures take place so close to home.

In Hook, Line and Sink Him, author Jackie Pilossoph turns the tables on the genre and hilariously chronicles the romantic mishaps of a thirty-year-old male protagonist, Jeff. In the novel, not unlike in a Shakespearean comedy, multiple couples break up and get together and a would-be lover teaches the woman of his dreams how she can trick another guy into proposing to her. The fun is seeing everything from a guy’s perspective.

Never mind that it’s a romantic fantasy–the story feels real because of the familiar settings. We meet the main characters in the wee hours at the sardine-packed Marie’s Rip Tide Lounge on Armitage, just a block away from where I used to live in Bucktown and, yes, I was once one of those sardines. Like Pilossoph’s characters, I’ve had dinner at Topo Gigio, I’ve had margaritas at El Jardin, I’ve played tennis at Midtown. Except for Cook County jail, I’ve seen just about every location named in the book.

Another reason the novel rings true is Pilossoph based the tale on her experiences dating in the city before she was married and the protagonist on a composite of all the commitment-phobic guys she dated. There were a lot, she says.

Jackie Pilossoph

Although we’re practically neighbors, Pilossoph and I had never met until I called her to ask about about her experience writing the book. She told me she started writing screenplays and submitting them to agents eight years ago. She came close to having a script optioned but the deal fell through. Then an agent suggested Pilossoph rewrite one script as a novel.

It turned out to be easier said than done. Pilossoph was divorced three years ago and had to work on her novel when her children were asleep, either late at night or early in the morning. There wasn’t time to join a writer’s group or take creative writing courses, let alone dwell on the irony of writing a book about finding the perfect match as her own life as a Mrs. fell apart. She just kept writing and in true romantic fashion her own story had a happy ending. On her blog, Pilossoph recalls being “completely giddy” when her publisher handed her the book, “hot off the press.”

If you’re looking for a light fun read, you’ll enjoy Hook, Line and Sink Him. It’s perfect for singles and divorced people who are on the front lines of the dating scene or for marrieds who just like peeking back at those crazy years from the other side.

Pilossoph told me she has plans for another book to come out in April 2011. I hope that one takes place in Chicago too. For more information, check out  Jackie Pilossoph’s website.

Read more Chicago Book Reviews.