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Most Regrettable Boyfriend and Girlfriend Tattoos in Dating History

We all make bad decisions.  We all do dumb things.  However, there are a select few people who decide to take things to levels that I will never understand.  Those people are the ones who are out there getting ridiculously bad tattoos of a lover.

I’m all for showing love.  But not via a tattoo!  A tattoo is permanent people!  And even if you want to go get it removed by a tattoo removal artist, that hurts like hell and it’s expensive.  I just don’t get the stupidity of people sometimes, and maybe it’s because I’m more of a casual hook up person and not really the type to profess love like others, but to me, permanent is permanent, and there is no turning back from a bad tattoo.  Today, I would like to give you my list of the most regrettable tattoos in dating history!

The Most Regrettable Tattoos in The History of Dating

This wasn’t an easy list to put together, and I spanned the web for the best (or should I say worst?) collection of tattoos that people regret.  If you have anything to contribute to this list, please by all means, comment on this and we’ll get it up there as well as with some proper credit to you.

My goal is to keep this current, fresh, and as zany as humanly possible.  I know I can’t possibly cover the entire world, as there are probably some bad tattoos over in Thailand or Costa Rica that I’ll never witness that just didn’t make it to the world wide web.  If you find them, send them.  Rewards may be given!

These are in no particular order, and I’ll keep adding to this list as I find more.  

The Replacement Tattoo

replacement tattoo

This first example is a guy who goes by the theme of “I don’t chase ’em, I replace ’em.”

Clearly, over time, this list could grow into a work of art, with many ex’s names crossed off the list.  This would be an interesting human to follow around and just see how far he really takes it.  I like how he clearly admitted wrong doing, by stating “oops” on the arm.  Tough break, Megan.

The List Guy

Well, as if this last find wasn’t a bit of “what could happen next” I don’t know what is.  This guy, who we will call the “list guy” did just what the replacement tattoo guy could do next.  He made a list of his ex’s and just kept adding to the list.  Don’t let the fair skin fool you.

This is a Latino, just look at the names of the women he’s been hanging with.  Or, this could actually be Kenny Powers back when he played for the Charros in Mexico.  We may never know, but what we can accurately predict is that Laura may be struck through one day and replaced.  My guess is that she will be either Juanita, Sara, or Juliana.  Any takers?

the list of tattoos guy

Nathan Ain’t Got Nothing on Ryan Wilson Tattoo

Wow, poor Nathan.  It’s bad enough that you go by Nathan, and not just Nate, Nate Dogg, or just something downright mean like Natron.  But now, you gotta live with being lesser than Ryan Wilson.  It’s in stone, Nathan.

One day you reigned as the king of her back.  Now, all you got is that your font is bigger than Ryan’s.  Hopefully that’s not all you got on him, but if you ask this woman, she’s got another opinion.

Nathan Tattoo


When Mary Turns into Marge Tattoo

Once upon a time, a guy dated a gal named Mary.  Mary and the guy broke up, and Mary became Marge Simpson on her knees cleaning up a mess.  The end.

I give this one an “A” for adaptability, awesomeness, and attention to detail.  Not many people would think of how to turn Mary into Marge, but this guy pulled it off and got a classic icon of a cartoon on his body in the process.

marge tattoo

The Dildo Tattoo

Some people know what they like.  They may not even regret this one.

dildo tat


Special Shout Out to TheThings.com who had most of these on their site and I used them.  Gotta give credit to the gang there. Damn, what a site that is. I  don’t give many shout outs but they are a great read, and game recognize game.  

The Brenda On Steroids Tattoo

Brenda’s got a baby was one of the songs that put Tupac Shakur on the map, and whenever I hear the name Brenda, I think of that song.  However, that all may change, thanks to this guy, who clearly loves Brenda.  Just, wow.

The Brenda Tattoo

The Naked Asian With a Great Set of Cans

I’m all for tattoos of naked women, but I don’t know about this guy.  He decided that he loved his gals naked rack so much, that he’d feature it front and center on his own chest.  Wow.  I’m officially speechless.

naked asian tattoo with big boobs

Shout to Ranker.com for the above gems.

What’s the worst tattoo you’ve ever seen someone get?  Whether it’s a hookup tattoo or a dating tattoo, just please don’t do it. Be smarter than that – really you’re better than that!

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