08/26/2011 03:14 pm ET Updated Dec 06, 2017

Gift Side Story Chooses Gifts For Your Girlfriend So You Don't Have To

Gift Side Story is trying to stop men from giving women presents they don't want by choosing the gifts for them. You just tell Gift Side Story about your girl's hobbies, her fashion sense and her interests, and the service responds with gifts that it thinks your girl will like.

Good idea? Great idea.

Good execution? Let's find out.

The folks that founded, designed and developed Gift Side Story think they know what women want. CEO and Founder Ankur Jain told HuffPost that Gift Side Story specifically can find "the right gift for the right relationship for the right event"; in order to do this, they need to get acquainted with your girl, her likes and dislikes, what makes her groove. Here's the initial survey you fill out that helps the Gift Side Story algorithm "learn" about the woman you're buying a present for:

After you fill out the profile of your gal, she shows up in your "gifting dashboard," a simple calendar that shows all of the days and holidays you have chosen that have significance. Here's the grid for my mother, which includes her birthday, Mother's Day and Christmas (but really Hanukkah):

You then receive an email in a few hours with three gifts that have been selected for you. You choose the gift that you think is the best match, and you can purchase the gift from the Gift Side Story website. The gift comes in the mail in the following days.

And that's it. In these early stages, it is a very simple site. Fill out a survey, choose from one of three gifts suggested for you, swipe your credit card and wait. Right now, the real story is how Gift Side Story chooses its gifts, and whether or not Gift Side Story is effective at offering the right gifts, which will likely determine the company's success going forward.

You might be thinking: How could a computer algorithm and a bunch of guys in Brooklyn that have (probably) never met your girlfriend possibly know what your girlfriend wants better than you can?

For learning about the girl and what kinds of gifts she might want, the most important part of the survey is the one in which you choose your girl's "style type," according to Jeff Jones, director of merchandising for Gift Side Story. Jones, who had more than 15 years of fashion wholesale experience before joining the Gift Side Story team as head gift chooser, said that the most difficult task of building GSS from the ground up was "categorizing every girl in the United States." Eventually, he landed on five different style types:

  • Bohemian (modeled after Siena Miller, with tribal patterns and animal prints)
  • Glam girl (modeled after Jennifer Lopez, with sequins and rhinestones, a girl who loves attention)
  • Suburban classic girl (modeled after an all-American, nautical, preppy girl-next-door)
  • Urban classic girl (modeled after Rachel Bilson, with black clothing that is tailored and fitted)
  • Eclectic girl (modeled after Gwen Stefani, loves "both thrift stores and Neiman Marcus")

These five types are depicted below. Try to guess which one is which:

Brainstorming for the style types was also difficult, Jones said, because he was going after so many different ages of women. In addition to selecting gifts for your girlfriend, fiancee or wife, Gift Side Story also works for mothers, mothers-in-law, sisters and friends, which the company believes covers the full range of women for whom you would invest in a good gift.

The gifts come in the categories you would expect: There are handbags and earrings, gourmet foods and personal electronics. Jones said that all of the gifts are made by boutique shops and that their catalog is updated every three months to include products (especially fashion accessories) that are in line with the latest trends. That way, Jain said, the guy can "look like a hero" when he gives a hot new gift to his girl.

It's a brilliant idea. Anyone who has ever disappointed his mother, girlfriend or sister with a present knows how much it stings (especially if you've ever disappointed them all on the same day); that an entrepreneur has come forward and automated the process, with a lot of research into what makes certain types of women happy, is a terrific boon to clueless (and, frankly, clued-in) men everywhere. The service is free to use, so even if you're just looking for suggestions, Gift Side Story is a great resource. It's a golden and original idea, and the process is idiot-proof, which goes a long way in the tech world.

But, like most startups in private beta testing (don't worry, we've got access for you, HuffPost readers), there is plenty of room for improvement.

First, let's talk pricing. The cheapest gift you can currently buy through Gift Side Story is $125.

That's right. The cheapest gift is more than $100.

The company is positioning itself, I suppose, as a luxury service. Right now, Jones and his small merchandising team are hand-choosing final gift selections for each customer to ensure that every suggestion they send out is just right. Jain said they had tried out a $50 price level (which was still around when I tested the site), but found that they weren't able to find gifts at that price point that lived up to their brand standard. This is just a hunch, but I'm guessing that they'll be offering products at a price much cheaper than $125 (and much cheaper than $50) when the general public catches on to their site, because most Americans just aren't spending $125 on Mother's Day presents. Gift Side Story can advertise hand-chosen gifts for their wealthier clients as a bonus for spending more, but they should just automate their service at lower price levels for middle class men like me who stink at buying gifts.

Second, there's some design work to be done. You'll see when you use the site that the interface is pretty barebones and rough around the edges. If I'm going to give my credit card to a website, I need that website to look like it has enough money that it won't be stealing my information. Right now, Gift Side Story isn't quite there.

Third -- and this is kind of heartbreaking, because I want it to work -- I got mixed reviews on the gifts that the site chose for the gals I filled out profiles for. My sister was pleased with the bracelet I would have gotten her, but my boss, HuffPost Tech Editor Bianca Bosker, was simply aghast at her three choices, saying that she would not be happy with any of them. In particular, if you were looking to get Bianca a gift for some reason, do NOT get her a pair of these, which Gift Side Story chose as her number one match:

Fortunately, Gift Side Story has a full refund policy. If your gal hates her gift, the company will refund your money plus shipping, pay for you to send the gift back to them and give you a discount on your next purchase (though I have to wonder why you would use them again if they had already failed at the one thing they profess to be experts at).

So far, Jain is reporting excellent satisfaction numbers, however, with only two returns out of hundreds of purchases. The algorithm is still learning; like Google's search algorithm, it gets smarter as time goes on, and Jain plans to speed up that learning curve by installing a Pandora-like "thumbs up-thumbs down" widget so that users can rate every gift suggestion they get. Another terrific idea: The site and the service are only as strong as the algorithm, and anything Jain can do to get early users to feed information into that algorithm is beneficial for everyone.

Gift Side Story is currently in private, invite-only beta, but you can get around the need for an invite and check out what Gift Side Story thinks your lady would like by navigating to this website.