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.
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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,
No.
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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!

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