5: How do I get that girl to quit chasing me around the playground asking for a Valentine’s Day kiss?

10:  This box of 25 Transformers Valentines comes with two extra-big ones. One of them goes to my teacher, obviously; is it awkward if I give the other one to the girl I have a crush on but haven’t told about that? What if she shows all the other kids, and then they’ll know I’m madly in love with her?

15: I know I need to get her roses, but do I need to rent a limo?

20: If I respond to a booty call on Valentine’s Day, will she think I think we should start dating for real?

25: How do I express precisely the right amount of proud defiance and sexy availability in a 140-character tweet?

30: Now that we’re engaged, can I start going a little easier on all this Valentine’s Day crap?

35: How do I pay for dinner when our babysitter is tripling her normal rates?

40: Should I be depressed that my five-year-old son, who I just caught playing you-show-me-mine-and-I’ll-show-you-yours with the neighbor girl, is getting more action than I am today?

45: Do I celebrate the signing of these divorce papers with one bottle of wine, or two?

50: How do I get my new girlfriend to spend Valentine’s Day with me instead of with the 32-year-old who’s sending her texts calling her “sweet mama cougar”?

55: What did her first husband do on Valentine’s Day? I need to top that.

60: She always talks about how she delivered her children with no drugs, so why is she pushing Viagra on me?

65: If we just go to the senior housing facility’s special Valentine’s Day meatloaf dinner, is that romantic enough?

70: Do I have to wait until the day after Valentine’s Day to tell her I don’t want her calling me “Alex Trebek” in bed any more, or can I tell her that today? Because I’m really getting sick of it.

75: Do I celebrate the signing of these divorce papers with one bottle of wine, or two?

80: If I respond to a booty call on Valentine’s Day, will she think I think we should start dating for real?

– Jay Gabler

Photo from Seibertron.com