As any man will tell you, buying gifts for any woman in his life — be it his wife, mother, girlfriend, daughter or sister — can be a tricky proposition. “I’ve had the problem many times where I wanted to be thoughtful, spent the time, but I just wasn’t sure exactly what to get her,” says Ankur Jain, a former private-wealth manager in New York who stepped up to the plate for his fellow men this August when he launched Gift Side Story ( Using an algorithm similar to Pandora’s, the site acts as an automated concierge that analyzes various details about your lady’s style (glam girl or bohemian?), home decor (modern vs. traditional), tech preferences (iPhone? BlackBerry?) and personality (blinged-out diva or pantsuited executive) to cull nine gift options — three specific to her and six more that similar women liked — sourced by director of merchandising Jeff Jones, a 20-year veteran of the fashion wholesale industry.

The site creates a boutique feel by featuring small-scale artisans and indie designers. Translation: handbag-like laptop cases from Brooklyn’s Kempton & Darrow and jewelry from Los Angeles–based designer Vanessa Mooney. And all products are accessible by photo and video. “Women will be aware of these brands, but most guys won’t,” says Jain. On the off chance the recipient doesn’t like the gift you choose for her, you can return it (free!) within 10 days. The site plans to add special-occasion gifts as well as implement a feature that will prevent two women in the same referral network from receiving the same gift.

“What a lot of gifting sites do is try to be everything to everybody,” says Jain. “Our calling card is helping guys find gifts for women. We’re trying to be the wingman for guys, so they can continue looking like a hero.”