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Objects of our affection

Forget the happy couple: The real star of the rom-com proposal is the engagement ring. Here, Neil Lane, the official jewelry designer for The Bachelor — or, as he puts it, "the most romantic comedy ever" — appraises the rocks in eight films that knew how to bling it on.

While You Were Sleeping (1995)

Lane's appraisal: A 1-carat classic round diamond, prong-set in gold, with an "arch" design around the band.

Estimated value: $8,000-$12,000

The ring Bill Pullman's Jack cheekily places into the token tray looks deceptively simple — which is why it's the perfect choice. After all, Jack caught Lucy (Sandra Bullock) off guard, winning her heart when she thought she belonged with someone else. "He got something that had a little style to it, instead of just a round band," Lane points out. "It's a beautiful, romantic ring with humility." And that's not easy for scene-stealing jewelry.

My Best Friend's Wedding (1997)

Lane's appraisal: A round-cut, 3- to 4-carat diamond, prong-set in a gold band.

Estimated value: $50,000-$75,000

It's no wonder Julianne (Julia Roberts) envied Kimmy (Cameron Diaz). Not only did the young, sunny Kimmy have the fiancé of her dreams, but she also had this ring, a timeless piece Lane says was fashionable when the film was released. "It's very classic," he explains. "These undecorated rings were still the trend [in the late '90s]."

Serendipity (2001)

Lane's appraisal: An elongated, marquise-cut diamond that's 5 or more carats, with two round diamonds on the side, all set in gold.

Estimated value: $100,000-$125,000

Everything about the ring Lars (John Corbett) chooses for Sara (Kate Beckinsale), which can be seen in this scene, is wrong — but that's the point. (She's meant to be with John Cusack's Jonathan, remember?) Sara had wanted a round diamond; Lars brings her something completely different. "He got the marquise cut, the opposite of the round," Lane says. "It's more triangular, with points on both sides. It was exactly the ring she didn't want." (Besides, it didn't fit!)

Sweet Home Alabama (2002)

Lane's appraisal: A square, cushion-cut solitaire diamond that's 4 or more carats, prong-set on a wide platinum band.

Estimated value: $150,000

Reese Witherspoon's Melanie Smooter — sorry, Melanie "Carmichael" — chose her own ring, thanks to Patrick Dempsey's Andrew (swoon!) shutting down a Tiffany's. "She picked out a ring that has a sizable impression," Lane says, adding that it matches the character's bold personality to a T. "It's a strong-looking stone with a wide band, so it's a solid ring. It's not wimpy. If she shakes your hand, you're going to see this ring."

Legally Blonde 2 (2003)

Lane's appraisal: A 5-carat, cushion-cut pink sapphire, with two 1-carat triangular side diamonds, all set in platinum.

Estimated value: $250,000

Once again, Reese Witherspoon's character scores a ring that epitomizes who she is. Just as orange would never be the new pink, Elle Woods would never accept a proposal without her signature hue. "Everything's pink [for her]," Lane says, "so she's gotta have a pink ring." But this ring isn't just pink; it's a pink sapphire, which means it's also one of the pricier options. Could Emmett (Luke Wilson) and Elle really afford something this valuable? "It's Hollywood!" Lane quips. Indeed.

The Family Stone (2005)

Lane's appraisal: A 3-carat antique European-cut diamond, prong-set in gold, with a vintage engraving.

Estimated value: $75,000

The film's titular jewel may be the oldest on the list. "It appears to have an engraving, which would indicate a vintage style from the 1890s, even 1920s," Lane explains. "It's wonderful they've been passed down, but in some families, [the wearer] doesn't love the ring." Case in point: Claire Danes' Julie tries it on — only to get it stuck on her finger. The solution? "Claire Danes can call me," Lane jokes, laughing. "I'll make her a new ring."

Sex and the City 2 (2010)

Lane's appraisal: A 10- to 12-carat round black diamond set in platinum with an undercarriage of tiny diamonds.

Estimated value: $50,000-$75,000

This unconventional ring — which Big (Chris Noth) presented to Carrie Bradshaw (Sarah Jessica Parker) — may not be the most expensive on the list, but it is, fittingly, the most sophisticated. (And so much more her speed than Aidan's — shudder — pear-shaped offering.) "Everything was fashionable in their lives," Lane says. "A black diamond surrounded by a halo of white diamonds is really chic. Nothing is more stylish."

Crazy Rich Asians (2018)

Lane's appraisal: A 15- to 25-carat emerald-cut emerald with 1.5-carat heart-shaped side stones.

Estimated value: $1 million+

Borrowed from star Michelle Yeoh's personal collection, this eye-popping emerald may seem like an unusual choice for an engagement ring, but colored gems are commonly used abroad, says Lane. Royals love them — Princess Diana's ring, now Kate Middleton's, was a blue sapphire — so why wouldn't Singapore's unofficial first family follow the trend? "That, in my perspective, took the film from 'Wow' to 'Oh, wooow!'" says Lane. Spoken like a jeweler.

Every day until Valentine's Day, Entertainment Weekly is celebrating our special romantic-comedy-themed Untold Stories issue. Check out all of our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram.

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