Don’t Get Surf & Turfed this Valentine’s Day: 5 Ways to Protect Your Wallet

valentine's day money saving

When I was 23, young, broke and stupid I learned this term. It’s when you generously take someone out to dinner on a budget and they unexpectedly order the two most expensive things on the menu, the steak and the lobster.

At 23, I was dating this guy whose pattern was to always split meals with me whenever we went out. He was a fairly skinny guy but he said to manage his cholesterol he wanted to split meals. He also didn’t drink or ever order desserts or appetizers. Needless to say, whenever we went out for a meal the bill was consistently low.

On Valentine’s Day I decided I wanted to mix things up and take him out. Stupidly, I chose to take him to the John Hancock building 95th floor Signature Room. I had never been, but I’d heard it was amazing. Did I mention I was 23 and broke? I looked up the menu beforehand but of course fancy restaurants often don’t list prices on the online menu. I figured we’d probably order one $35 -50$ entre and share it like we normally shared meals. There’d be no appetizer, drinks, desserts etc. because he never wanted those things anyway.

When we got there, it took him all of five minutes to order the most expensive appetizer on the menu, the lobster seafood platter. When it was time to order entrees, the waiter informed us that we must order one entrée per person, there would be no sharing at this establishment. I ordered the chicken, the cheapest menu item. He ordered the most expensive steak. I cringed. Dinner was followed by $15 dessert and $9 coffee. The bill was $200 plus 10% tax plus 20% included gratuity, for a grand total of about $260. Did I mention I was 23 and broke? As I swiped my credit card I said a small prayer that it wouldn’t be declined. I’d just spent a car note on dinner.

To add salt to the wound, in the car ride home he commented that dinner really wasn’t that great. A month later we broke up, not because of dinner but because the entire relationship was a hot freakin’ mess.

If you are married or in a really serious loving committed relationship and you want to spend a car note on dinner for an amazing experience with your significant other, then that is awesome and more power to you. But if you’re newly dating, or dating for a while but still learning a person then pace your efforts and your wallet. Here are 5 ideas for an awesome Valentine’s Day that doesn’t break the bank.  Valentine’s Day & Tuesday Night Dishes

  1. Stay in and cook dinner. Make it special by playing music, lighting candles, and dressing up. Don’t underestimate the intimacy of a home cooked romantic dinner. Top off dinner with homemade baked goods (a pie, a favorite cake, etc.
  2. BYOB is your friend. Go on Yelp and find an eclectic BYOB that your partners never been to. My favorite BYOBs typically have entrees priced at $8-$12 yet the food is amazing and the ambiance of the space make it different and special. Furthermore, at a BYOB your tab won’t get ran up by alcohol and you can impress your date with your knowledge of wine. (They don’t need to know the wine you brought was from the $8-$12 shelf…also Trader Joe’s is your friend.)­­
  3. Skip dinner and hit up a dessert bar. At a dessert bar, you can order a slightly overpriced sweet treat and share it to save calories. No one will think you’re cheap for sharing dessert. Most dessert bars also serve wine, cocktails and coffee so you can sit for a bit and enjoy each other’s company.
  4. Sample the Best – Tell your date for V-Day you will be taking them around the city to try “the best” of things. Start with appetizers at a favorite spot (i.e. lobster mac and cheese at Del Frescos, shrimp tacos at Del Torros, Tiramisu at Artopolis….a few of my Chicago favorites) , and keep hopping spots through dessert and after dinner drinks. At each place order, something small and share it. It’s as if you are having Tapas but in several places. The trick is you have to have everything really well planned, including transportation and reservations. No one place needs to be fancy, just delicious and convenient.
  5. Be Sentimental / Recreate the 1st date – Chances are wherever you went on your first date probably wasn’t expensive. On my first date with my husband we went to breakfast and then took a walk. It’s too cold for the walking part but we could do breakfast for dinner. Recreating the first date is special because it’s sentimental, but it’s also not going to break your wallet.


Good luck and have fun! Don’t forget to report back and share how the night went. I’m excited to hear your stories of fun loving and frugality!


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