Book Review: Dear Bumbling Boy

Reviewed by Joelene Pynnonen

 A wry, relatable dating memoir in which the suitor is also a prospective character study.

When author Jenny Dee’s online dating encounters repeatedly ended in disappointment, she realized that there was more potential to the trainwreck matches she’d been getting. Viewing the texting, phone-calls, and dates as fodder for her writing, Dear Bumbling Boy was born. 

In this part dating-memoir, part character-study, Dee captures much of the essence of the modern online romantic experience in all of its horrific, hilarious, and confusing glory.

Dear Bumbling Boy feels like a cozy, amusing conversation with a close friend. It’s light, wry, self-deprecating at times, but never mean. For a book titled Dear Bumbling Boy, Dee is candid about exactly where these dates go wrong. She goes into the experience with an awareness of her own insecurities and foibles, so it doesn’t feel as though she’s indiscriminately criticizing everyone else. If she’s the one who messed the date up, she’ll own it. 

Many of us have had some experience with the world of online dating, so there’s an element of recognition while reading through some of these encounters. The endless texters, the gaslighters, the ghosters. What Dee brings to the table is the humanity. She sees the bits of personality that often go unnoticed in these scenarios and shines a light on them. 

Going into this, I was prepared for a wild ride of terrible first dates and bumbling fools. And, yes, a few of those scamper across the pages. Like the chef who showed up in the dirty sweatpants he’d worked the day in and spent the night complaining about child support. But many of these dates, while incompatible, are genuinely sweet and portray an authentic bonding experience with Dee.

The format of Dear Bumbling Boy does get a bit repetitive as the book goes on. While it’s set up as a kind of dating memoir, it also works the angle of seeing the potential suitors as characters in the author’s future works. 

As such, the relationships are broken into subsections. “How Far Did He Make It?,” “The Backstory,” “Classic Line(s),” “Future Character Attributes,” “Role I Would Assign Him,” and “My Takeaway.” For several of the paramours, these captions work. Each adds a more delicious layer to the character/date in question. 

However, there are many where there is little of substance to add to the caption. A surfeit of dates that the author wouldn’t assign a role to, for example. After reading about thirty dates set out in the same manner, they can blend into one another. 

I love the idea behind this dating memoir. Fresh, funny, and all too relatable. It delves into the awkward, fumbling trials of modern love and puts some of the warmth back into it in the process.

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