Relationship Retrospective: Drew Barrymore’s Past Loves

Drew Barrymore: wild child, movie mogul…wife and mother? It seems like just yesterday that she was flashing her boobs to David Letterman, but our Drew is finally all grown up, engaged to the ultra-hot Will Kopelman and reportedly preggo.

So I got nostalgic for the long and convoluted history of Drew’s love life, which includes two past marriages (one that lasted a month!) and countless other paramours. Let’s take a look back at the most notable real-life leading men of my all-time favorite serial monogamist.

1 of 8

Drew Barrymore and David Arquette

Back in her natural-eyebrow days, circa 1991, Drew made the rounds with David Arquette. Based on his still-solid relationship with now-ex-wife Courtney Cox and his general adorableness, I'm an unabashed David fan. From a puppy-love standpoint, he's pretty ideal.

Grade: A-
drew barrymore, jeremy thomas, marriedPhoto: Bollywood Celebrity Gossips
2 of 8

Drew Barrymore and Jeremy Thomas

Back when she wasn't making the wisest decisions, Drew got hitched to this guy Jeremy Thomas, a bar owner. Somehow it doesn't surprise me that she hired someone from a psychic hotline to perform the ceremony. I don't have enough information to either approve or disapprove of this relationship, but there's something about him that just rubs me the wrong way.

Grade: D. Why not F? Eh, he's kinda cute.
drew barrymore, eric erlandson, relationshipPhoto:
3 of 8

Drew Barrymore and Eric Erlandson

This is one of my favorite Drew incarnations: the spikey-haired free spirit of the mid-90s. Her beau at the time, Eric Erlandson, may not have been marriage material, but at that point Drew wasn't either. Eric looks sweet enough, and she seemed pretty happy with him (look at her face!), but he also happened to be a member of the band Hole, meaning Drew spent a lot of her time prancing around with the erratic Courtney Love back then.

Grade: C, for the Courtney Love influence alone. (Sorry, Eric.)
drew barrymore, luke wilson, relationshipPhoto:
4 of 8

Drew Barrymore and Luke Wilson

Who remembers Home Fries? Anyone? Aside from starring together in a movie no one saw, Drew and Luke seemed like an adorable duo, and this relationship marked the beginning of her eventual transition from wild child to sophisticated style and business icon. The relationship only lasted a couple of years, but we think it changed Drew for the better.

Grade: A. We miss these two together.
drew barrymore, tom green, marriage
5 of 8

Drew Barrymore and Tom Green

Oh, boy. I like to think Drew was suffering from a blow to the head when she hooked up with this loon -- and married him, no less! I get it, Drew. You like to have a good time. You like guys who make you laugh. So do I. But this dude will forever be the worst relationship decision you've ever made, and I almost have never gotten over it.

Grade: F. Double F!!
drew barrymore, fabrizio moretti,
6 of 8

Drew Barrymore and Fabrizio Moretti

Drew likes 'em cute. Can you blame her? When she started dating The Strokes' drummer Fabrizio Moretti in 2002, I was all "go, Drew!" And then they lasted for five years and seemed quite cozy and normal for a rock-n-roll couple. I was hoping for a ring -- but, alas, got a breakup announcement instead. This one was a heart-sinker.

Grade: B+, only because he didn't marry her.
drew barrymore, justin long, relationshipPhoto:
7 of 8

Drew Barrymore and Justin Long

Just look at these two. Adorbs, right? The Mac guy, as he'll always be known to me, seemed like a loving, stable influence for a wiser and more self-possessed Drew, and it looked like he genuinely loved her. These two were on and off for about three years, but ultimately the good guy finished last. *Tear.*

Grade: A+ Love him.
drew barrymore, will kopelman, engaged, married, pregnantPhoto:
8 of 8

Drew Barrymore and Will Kopelman

Hmm, I'm not sure about Will yet...but I like that he put a (4-carat!) ring on it. Also worth noting: the fact that she may be pregnant. Please, let this marriage stick and not fizzle out post-baby. I want to like you, Will. Don't disappoint.

Grade: TBD. This one-woman jury is still out.

Jonesing for more celeb roundups? Check out my Top 10 Train Wreck Couples of the past year.