If you’re like most of us, you’ve been on at least one side — if not both sides — of an expensive date that turned out not to be worth it. Here are just a few examples where the price wasn’t a good return on our daters’ investments.

Overpriced Date #1: A meal at the new “hot spot”
Margaret Marcus was dying to try a very “hot” new restaurant in New York City. So she and her boyfriend made reservations two months in advance — which were required by the establishment — and waited. “All the anticipation and good reviews made us even more excited about trying this place,” she recalls. “By the time we got there, our expectations were incredibly high. Sadly, there was no way this place could live up to them. The food was great, but it was too loud for a good conversation and the service was slow. So in all, it was a disappointment. And it cost us $300.”

Lesson learned: You can avoid dating heartburn by managing your expectations and focusing on exploring something new with your date — not the material cost of the date itself.
Browse Local Singles at Match.com on Yahoo!
Overpriced Date #2: Tickets to a sporting event
“My girlfriend is a rabid college hoops fan, so I scored tickets for the opening round of the NCAA so she could see her highly ranked alma mater play,” says Mark Vanetti, a self-proclaimed “Washington bureaucrat” in our nation’s capital who spent about $500 on the treat. “Unfortunately, her team was upset in their first game and bounced from the tournament. She was upset with the team — and a little upset with me, too.”

Lesson learned: You can snatch your date from the jaws of defeat by avoiding situations where emotions are already guaranteed to run high — and crash even harder.

Overpriced Date #3: A day of pampering
Lori Marcoux, a personal coach in Seattle, WA, treated a date to an extravagant resort and spa experience, but her date didn’t seem to appreciate it: “It was so foreign and insignificant for him that I regretted spending the money. Planning a camping trip would have been more his thing.”

Lesson learned: You can skirt a pain in the paycheck by planning dates that fit better with your date’s personality and interests.

When is an expensive date worth it?
“Sometimes the more expensive dates are absolutely worth all the hype, but this is only when the hype is about surprising the other person with something that means something to him or her,” says Marcoux, co-presenter of Extraordinary Couples — Accentuating The Positive through Extraordinary Learning, the company she co-founded. “The cost must be less relevant than what I think is the most important issue: helping the other person feel special, letting your date know that he or she is worth the effort, worth the expense, and worth every thought that becomes evident as a new delight that was obviously chosen with your date in mind presents itself.”

The key, Marcoux says, is to focus on connecting with your partner through the date. “Dating only works when it’s about getting to know a potential mate while helping that person understand you better,” she continues. So when you’re thinking about a date — be it extravagant or otherwise — plan activities with the other person in mind while satisfying your own needs at the same time: “Be creative, respecting what works for the other person while respecting what works for you at the same time.”

Taking failure in stride
It’s also important to not make an already bad situation any worse, especially if you or your date sincerely tried hard to create a great experience or if just one of you enjoyed it. “We want to learn how to have a good time in spite of some of the bad choices we make by thinking we know the other person well enough to pick the ‘perfect place’ for the next date,” Marcaux explains. “It’s up to me to not have a bad experience, regardless of whether I am spending big bucks or no bucks.”

The next time you’re planning a big date, keep these tips in mind:
  1. Don’t let the material aspects of the date overshadow the connection you want to make with your date.
  2. Keep everyone’s expectations in check.
  3. Choose dates that don’t involve too much built-in emotional investment.
  4. Plan activities that will appeal to your date, not just impress your date.
Finally, remember the words of philosopher Friedrich Nietzsche: “What doesn’t kill us makes us stronger.” Instead of beating yourself (or your partner) up emotionally about an expensive date that failed, use it to strengthen your bond — after all, you got through it together!

Margot Carmichael Lester is a freelance writer living and working in Carrboro, N.C.