Valentines Day Cartoons

Only 2 weeks now until Cupid’s big day! So, to get you in the mood, I thought I’d share some recent Valentine’s Day cartoons!


I thought of this cartoon early one morning and had to keep repeating it to myself under my breath to remember it.

This is actually pretty much how I, and I suspect most men, shop for cards. Not being comfortable with the flowery romantic stuff, we tend toward ones including the words hubby with cartoon bears that fold out like an accordion.

I’m betting the Mrs. would prefer something mushier, but, especially when you marry a cartoonist, goofy usually wins out.

(BTW, you can watch a video of me sketching this cartoon here.)


I thought of this because it’s impossible to think “box of chocolates” without thinking “life is like a.”

It’s annoying and irritating, sure, but instead of pushing past it, I decided to embrace it and finally define exactly what you’re going to get.

You’ve got your basic chocolate, your thin disappointment, your renamed knockoff (I’m looking at you, “tortoise” candies), and, my personal favorite, white.

Now you know.


This Valentine’s Day cartoon was a bit of a trick. Te idea is that more than one arrow makes the person a stalker instead of just in love. So, you have to make the guy look like something is wrong with him, but not so disturbing that the cartoon goes from funny to creepy.

After scanning in the original sketch, I spent a good amount of time in Photoshop tweaking things to get what I hope is juuuust the right expression. I hope I got it, I think I did.

Also the Cupid’s name changed a few different times. He was Larry (too funny name-ish), Lloyd (too Gary Larson-ish), Bill (not funny enough) and Phil (used too often in other cartoons). But for some reason when I was typing in the caption, Stan just worked.


This is another take on getting away from Cupid. I’ve done some more standard heart themed cartoons before (heart as organ, heart as playing card suit), but this is a decidedly different tack, heart as flowchart shape!

I actually had to look up some flowcharts to see how they looked and worked (it’s been a while), and I think this one looks complicated enough to make sense for the gag, but not so complicated that it doesn’t read quickly.

One thing I noticed almost too late was that the name I’d used in the caption started with a different letter than either of the first name initials in the heart, so I had to make a last minute change to “Debbie.”


Recently I’ve been playing with the new iBooks Author, and there’s been a bit of a kerfuffle over Apple’s EULA. Some people assume Apple is trying to make some sort of giant content grab, others assume it’s less onerous. Either way, it got me thinking about EULAs in general, and this cartoon popped out.

I think it totally makes sense that before someone shoots you in the heart with an arrow that there would be some sort of legal paperwork, and kudos to Cupid for using an iPad!

Well, I hope these get you in the mood for the big day! Feel free to check out all of my Valentine cartoons, and don’t forget to use the decoder!