It’s been a brutal few months for celebrity romances. At last count, 11 married or engaged well-known Hollywood couples have called it quits, and it seems like each break-up has been a little harder to handle than the last. Now that the summer is winding down, here’s a look back at the engagement rings (and couples) that we’re sad to say goodbye to. Also: Here's hoping that anyone who wore these rings is in a happier place now!
SEPT. 2: Avril Lavigne & Chad Kroeger
Chad initially proposed with this massive pear-shaped diamond. He presented his bride with an upgrade ring, also huge, on their one-year anniversary.
AUG. 19: Megan Fox & Brian Austin Green
Even before they were married, Megan often paired her engagement ring (a radiant-cut diamond in a halo setting) with a thick band.
AUG. 4: Zayn Malik & Perrie Edwards
First Zayn parted ways with One Direction, then he parted ways with fiancee Perrie Edwards. The two announced their engagement in the summer of 2013.
Zayne proposed with this three-stone ring, which Perrie wore on the red carpet to casually announce their engagement.
AUG. 3: Reba McEntire & Narvel Blackstock
The longtime country couple (26 years of marriage and 35 years of working together) split despite daughter-in-law Kelly Clarkson’s attempts to get them to reconcile.
Reba’s ring featured a large round-cut diamond with channel-set diamonds on the band.
AUG. 3: Gwen Stefani & Gavin Rossdale
Fans were floored when the musicians announced they were splitting after 13 years of marriage and three children. The couple said in a statement that they “remain partners in parenthood and are committed to jointly raising our three sons in a happy and healthy environment.”
As we’ve discussed, Gavin proposed with a thick black band with diamonds, but shortly after they swapped vows Gwen started wearing a squat pear-shaped diamond in a halo setting.
JULY 20: Blake Shelton & Miranda Lambert
Post-wedding, Miranda paired her engagement ring—a three-stone ring with more diamonds on the band—with two diamond bands.
JULY 14: Sienna Miller & Tom Sturridge
After four years together, the couple, who are parents to three-year-old daughter Marlowe, did call off their engagement—but don’t rule out a reconciliation. It’s been reported that they “intend to remain great friends,” and they’ve been spotted out together post-split.
Sienna’s art deco-ish engagement ring appears to feature a bezel-set round stone.
JUNE 30: Jennifer Garner & Ben Affleck
Souls. Crushed. The A-listers split after 10 years of marriage (they announced the news the day after their 10-year wedding anniversary, in fact).
Jen’s ring featured a huge cushion-cut diamond flanked by trillion side stones, which she paired with a plain metal band.
(These didn’t happen in summer, if you’re going by the calendar. But since they’re after Memorial Day, we’re counting ’em.)
JUNE 17: Charlize Theron & Sean Penn

During one of their last public outings, Charlize wore this massive pear-shaped diamond on THAT finger.
JUNE 12: Emma Roberts & Evan Peters
Emma’s ring featured a round diamond in a delicate rose gold halo setting.
MAY 28: Chris Soules & Whitney Bischoff

Neil Lane himself said Chris was “effervescent” when he picked out this four-carat sparkler for Whitney, which has a three-plus-carat center stone center stone surrounded by a halo of 20 brilliant-cut diamonds and 94 more diamonds in the band.