A New Valentines Day Dinner

February 13th, 2013

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Men of Boston. Tomorrow is Valentine’s Day.

I KNOW! SURPRISE SURPRISE! WHAT A SHOCKER!

V-Day is back and ready to make you look like either a glowing stud, or an insensitive little jerk. Here’s how to avoid the jerkness, and up the studness. WARNING: If your girlfriend / boyfriend, whatever, is super traditional… then you should probably stick with candy, flowers, and a sit down, boring dinner. HOWEVER, if your significant other is cool with new experiences and switching things up a bit… continue reading.

Last year, a very good friend of mine named Brian Shelley (an unbelievable part-time CFO, if you’re looking for someone to help you with your financials) told me about this little secret, and I took his advice. He said: “Ryan. If you don’t have plans yet with the lady for tomorrow night, and you are looking to do something different and fun, take my advice: Skip the Valentine’s Day dinner, and bar hop instead. You’ll thank me later.” And guess what. Last year was the best Valentine’s Day I’ve ever had. I got to skip the frustration of reservations, lines, price gouging, parking, etc. Instead, I had an awesome night. Here’s my recommendation to you.

WHAT TO DO

1. Have a light meal at home around 6 PM. Perhaps a grilled cheese sandwich, or something. Then, at 7 PM, take the T or cab into Back Bay / Copley / the Pru.

2. Pick out 2-3 bars you and your lady have always wanted to try out, and maybe 1-2 classics you guys frequent often.

3. Bar hop from one to the next.

Here is my Back Bay rotation this year, as recommended by Brian Shelley yet again. All of these are within a short radius to one another:

Oak Bar – One of the coolest rooms in Boston. Remodeled just this past year. It’s a definite.

City Bar – Cool small/dark spot located in the Lennox Hotel.

Lolita – Neat vibe, especially for V-Day. Lot of red.

Towne – Nice spot.

Top of the Hub – Another standard, but might be jammed.

Recommendation: If you want to make sure you don’t pick crappy bars, do some research before hand. Tell your g/f or b/f why you picked each bar. Wrap a little story into the night. Then, have one drink at each place, and make it a rule that each drink has to be different. Or force each other to pick out drinks for the other person. Whatever you do, just have fun with it. Bar hop! Do it at your own pace. Have a romantic night together. I promise you you’ll have a spontaneous night that’s fun, interesting, different, and completely not what you expected out of a traditional Valentine’s Day.

Good luck! Have fun! Make. Me. Proud.