“You wouldn’t necessarily know how awesome this place is from the front of the store,” Julie says. “But part of the joy of shopping is the exploration.” In the back, there’s an entire selection of antique magazine ads and vintage photos. For bride Rachel, Julie finds a 1924 silverware ad from Ladies’ Home Journal ($13). Andrew gets a 1964 black-and-white snapshot of a cabin ($1.50), while Lauren gets a notepad with a picture of a woman in a vintage swimsuit ($7.50).

At Laurie’s Planet of Sound (4639 N Lincoln Ave, 773-271-3569),  Julie immediately enlists the staff to find jazz or punk on vinyl for Andrew. Before long, she’s got two jazz albums (Miles Davis and Dizzy Gillespie, $5.99 each) and a Dead Kennedys T-shirt ($14), plus the ’80s teen flick Pretty in Pink on DVD ($10.99) for Lauren. (“I was a 16-year-old girl once, and that’s a classic. And I’m not gonna lie: I did have quite a crush on Andrew McCarthy.”) Inspired by finding Bitch magazine at Laurie’s, she snags a year’s subscription card ($15) for Rachel, reasoning the mag is a badass counterpoint to the ’20s silverware ad.

Next, Julie hits the Book Cellar (4736 N Lincoln Ave, 773-293-2665), hoping to score a swimming-related book for Lauren. No luck. With time running out, dissatisfied Julie spends the last of her budget on Divine Secrets of the Ya-Ya Sisterhood ($13.95) instead. The novel’s not new, she frets, but she hopes it will be fresh to a 16-year-old.

“The thing about thoughtful gift-giving is: You shouldn’t do it rushed,” Julie says. “If you don’t have a well thought-out shopping strategy, you often just end up with stuff, especially at Christmastime.”

Her favorite personalized ideas that don’t cost much include making a mix-CD; tracking down a recipe for a person’s favorite dish from a beloved restaurant; or buying a book and then taking the recipient to meet the author at a local bookstore. “Thoughtful doesn’t mean expensive,” says Watson, who spent $88 on her spree. “There’s a lot of things that aren’t expensive, but they’re really cool.”

The verdicts
Rachel “I love this shopper! I would definitely frame the silverware ad for my kitchen or dining room. And a subscription to Bitch, my favorite magazine? Love it.”
Andrew “The Miles Davis album is a nice pick. And the Dizzy Gillespie album: Holy shit! The T-shirt, I’d wear now and then. This shopper definitely did the best job.”
Lauren “Cute, girlyish gifts. I would enjoy them.”