Ask Dirk: A North Valley guy’s perspective on relationships

Ask Dirk

A North Valley guy’s perspective on matters of the heart and home.

Dirk,

Blessing be upon you M.D., I hope this message finds you well. I’m writing to ponder your thoughts on asking my lady to take my hand on Valentine’s evening. My plan is to ask her to take me, to have and hold, between dinner and dessert, and have the server deliver the tiramisu with an engagement ring in the top layer of custard, and just leave the diamond poking out the top. I have read enough of your terrible first date stories to know you have some experience with bad romance, so I thought I’d seek your “expert” advice.––A Hopeless Romantic

Hi Hopeless,

Ok I am just going to jump right in here––NO, that is a terrible idea. Let’s say she says “yes,” best case scenario. I was a waiter for a decade during college (it took me a long time to get no degree). Ain’t nobody got time for all that. Valentine’s Day dinner service is going to be a madhouse for food servers––don’t try to recruit them to do your 80s John Hughes’ film romance fantasy.

Second, it just seems like you are trying to dodge a bullet by giving yourself an awkward public set up. What if she says “no” (I would)? Are you just going to sit there and eat around the stone in your dessert, get distracted, and choke to death on the irony? Ask her if she wants to re-watch Lost after dinner?

Third, and finally, do you really want to place something so meaningful on top of another holiday? One generally associated with fighting a mountain of high school lovebirds and forgetful husbands who didn’t think they would need a reservation to the Olive Garden on a Tuesday…? Don’t be that guy. As you pointed out in your letter, I have already blazed the trail for you.

––Dirk

10 Terrible Places to Propose

The following list needs no explanation as to why they’d be awful spots to propose. If you need to ask why, you shouldn’t be asking the BIG question.

10. The same place you proposed to your first wife
11. In a tattoo shop
12. On an airplane
13. On television
14. In a parking lot
15. On social media
16. In the jewelry store after buying the ring
17. In a shady motel room
18. At a fast food restaurant
19. In a delivery room