Wednesday, April 28, 2010

Day 17: "Dear Caleb" Sweet Samplings

I had some early entries for my "Dear Caleb" advice column, and thought I would answer them and post so that you might get an idea of my wisdomosity. These are real stories, with only names and distinguishing remarks left out.

Dear Caleb,
I am currently dating a girl but plan on breaking up with her. She's nagging, whining, jealous, and went from the fun person I knew when we dated to an evil she-demon now that we're official. I was planning on waiting until after Prom this weekend to break up with her, but I was wondering if I should just do it now. What should I do?

- Inevitable Procrastinator in Iowa

Dear Inevitable,
Can you get a hummer from someone else if you dump her now? That's the question you need to ask yourself. If you are convinced that your wiener would remain dry and un-slurped if you were to go stag, then hang on to her for the weekend; no sense giving up your prom-desert. If, however, you think you have the slightest amount of game then dump her now and free yourself up for some prom girls (think sexy underwear, hot dresses, and low self-esteem). Plus, you'll have a dashing combination of confident decider on the one hand and slightly wounded and vulnerable recently-broken-up-with sad guy vibe on the other. It'll be like someone tied lead weights to the bottom of every girl's panties for you, guy. Make the right call.

Dear Caleb,
My boyfriend and I recently upped our sex life by orders of magnitude and are now getting it on way more often than we used to. Does this mean that I can stop giving him bjs?

- Humping in Hartford

Dear Humping,

And now for the word of the day: shenanigator. Noun. Person who instigates shenanigans. Some shenanigator just tried to order 6 whoppers from the McDonalds drivethru window!

Use it as all you want.

Happy hump day!

PS go be ironic and do some actual humping today. You know you want to!


  1. this is probably my favorite post thus far...well done, sir, well done

  2. Thanks Kayla! You should send in something to the Dear Caleb inbox at! I'll give you a featured spot!