02/06/2014 03:47 pm ET | Updated Apr 08, 2014

The Art of the Ask: 3 Tips to a Yes This Valentine's Day

If there's one thing Valentine's Day proves, it's that Americans are in love with love.

Our national obsession with romance and marriage is alive and well. According to American Express' Spending and Saving Tracker, six million couples became engaged on Valentine's Day 2013. The National Retail Federation reported that $18.6 billion was spent celebrating Valentine's Day in 2013, about $131 per person. Destination wedding budgets are up and the industry of honeymoon tourism is at an all-time high. Even TV's favorite salute to courtship, The Bachelor, opened its new season with its highest ratings in three years -- up 17 percent from last year.

And with a whole new constituency allowed to get married, record number of proposals are anticipated this Valentine's Day, but how many will be successful in their "Art of the Ask"?


Demystifying the process isn't that complicated. People are afraid of a "no" -- so how can you be sure of a yes? Here are three simple steps to getting your nearest and dearest to accept your proposal.

Step 1: Know Your "No's"

Unless you're completely clueless about the state of your relationship or that your intended has absolutely no interest in a long term situation, rarely is the initial "No" definite. "No" can mean many things:

  • Not now, too soon, I need more time. (Response: I'm in no hurry, I'll wait.)

  • Maybe, but I'm scared. (Response: I'm scared, too.)
  • Not sure how you feel. (Response: I've never been more sure of anything in my life.)
  • Not sure if it financially makes sense. (Response: Let's sit down and try to make a plan.)
  • There's a religious/cultural issue. (Response: If we truly love each other, we can work this out.)
  • I don't want you to meet my parents/family. (No one wants a potential partner to meet their family, all families are weird.)
  • I have a "secret" I don't want you to know. (Everyone has secrets, no one really cares.)
  • "No" is such a shattering word that upon hearing it, we sometimes crumble, and fold our tent. Don't let go so easily. Effective probing is a technique that salespeople have used for many years to get customers to buy their products. Getting someone to commit to your relationship is a form of salesmanship. Find out what's really going on, and then strategize to seal the deal.


    Step 2: To Thine Own Self Be True

    The trappings of Valentine's Day can be seductive: candlelight, flowers, candy, perfume, jewelry, a romantic restaurant -- all set the stage for the ask, but are you truly committed?

    Reasons for "Yes" do NOT include, "It'll be fun," "We can always split later on," "I don't like being alone," "He's/She's so hot," "He's/She's the best that I can hope for," and many other such ambivalent declarations. A true self-inventory needs to take place before the Valentine's Day blitz. A lawyer friend of mine once told me that in court, you never ask a witness a question you don't know the answer to. In this case, if you are honest with yourself and clear about your feelings, odds will dramatically increase in the "Yes" column.


    Step 3: Be Prepared (for the "No")

    Animals who live in the jungle all know that fear has an odor and they can smell it a mile away. Same holds true for potential partners.

    Nothing can dampen a potential romantic partnering more quickly than the smell around the fear of being rejected. I am not a believer in the adage that for each person there is a one true mate. There are plenty of man/woman, man/man, woman/woman combinations out there and you have to go into the ask, as scary as it may seem, with the possibility that your potential partner will decline. It's like skiing... the first thing I learned when I was taught to ski was how to safely fall. Isn't that the biggest fear about skiing -- falling and hurting ourselves? When you learn how to fall the right way, there's nothing else to be afraid of, so as your skills increase, you ski with even greater confidence.

    So, this Valentine's Day, if the worst thing that can happen is for you to hear "No," then be sure you're prepared for this eventuality. It takes two remember -- and as my grandmother used to say, "Unrequited love is a bitch." If, at the end of the day, you can handle, "No," you can go into the conversation with greater confidence, thus increasing the chances of "Yes."

    AND, if it turns out to be "No," you can turn it into a "Yes" with someone else more suitable... and I'll take that "Yes" any day!


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