Men who look like old lesbians

David Cassidy is one of my favorite men who look like old lesbians!

I’ve been hiding this blog about men who look like old lesbians under my hat for awhile now, but the internets are all abuzz with the phenomenon yet again, so it’s time to share.

As the gender line becomes more ambiguous and we all start swapping jeans, it’s not unusual to be unsure of who you’re looking at or what they’re trying to say with their appearance, especially in this town.

When you combine this factor with aging 90s haircuts and fashion, sometimes it can go terribly wrong. (I’m so sorry to be looking at you Dana Carvey.)

And while straight up top 25 men who look like lesbians posts exist, I’m going to give you just a few of my favorite faces and explain how they fit the spectrum in my snarky opinion.

Jake Gyllenhaal

Cutest man who looks like a lesbian: Jake Gyllenhaal looking a little like Kate Moenning (The ‘L Word’s Shane)

Anyone who knows me or reads this blog regularly understands my obsession with the Gyllenhaals, especially my Jakey. So this was an ultra-biased given. But c’mon! Man, woman, straight, gay, he really is just beautiful isn’t he?

Ugliest man who looks like a lesbian: Stephen King

I really really wanted to choose Don Imus. He just looks like a really nasty old woman. I guess years of being a shock jock can really wear on you. But despite the fact I value his writing, both the cheesy and the literary, Stephen King does not an attractive woman make…

Stephen King and Don Imus

Best Pacific Northwest celeb (man) who looks like a lesbian: Chris Willa

Washington based lead-singer for Death Cab For Cutie, indie rocker Chris Walla’s picture holds the very appropriate caption, “OMG! I got tickets to Ellen!”

Richard Marx

Most intense man who looks like a lesbian: Richard Marx

The 80s power-ballad style metal hair is just too much. Haven’t I seen you at the E Room?

Best male child actor who looks like a lesbian: Corey Haim

It was a real toss up between Mark Paul Gosselaar and the Coreys, who have been mentioned several times in the blog. But although Mark Paul wears the PICA Kristy Edmunds black turtleneck so well, I just gotta go with the super-butch and badly tattooed Haim. (What does this say about my view of lesbians?)

Corey Haim and Mark Paul Gosselaar
Chuck and Mo

Best hipster glasses on a man who looks like a lesbian: Chuck Klosterman vs. Mo Rocca

Adorable. I love glasses. And Richard Butler came in a very close second. Do I need to say anything more?

Craig Williams

Most lesbionic man who looks like a lesbian: Craig Williams

I don’t even know who this guy is but he really really looks like a lesbian. I think he wins the contest overall.

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