Sasha Speaks: Answering Your Most Private Dating Questions — The Other Shoe?

  • Posted on: August 15th, 2011 by

Dear Sasha,

I’ve been dating this guy for around 2 months now. He’s almost too good to be true, and I keep waiting for the other shoe to drop. Am I just a jaded dater or could he really be that perfect?

Waiting for the other shoe to drop?

Dear Shoe Dropper,
It sounds to me like you’ve had one too many heartbreaks and you might be steering yourself toward another one, not because this guy has a hidden agenda, but because you’ve grown cynical.

Remember the good ol’ days of youth when “I love you” meant something? When “going with” someone was as sacred as getting married in the Vatican with the baby Jesus as your ring bearer? When a first date was the start of something new and exciting and magical?

Yeah, I can’t really either. But I know that at some point in my life I did feel that way.

Dating is hard and, the older you get, it only becomes more difficult. Having tried everything from late night bar hookups to an internet algorithm to find romance, I’ve been on more horrific dates than any person should ever have to suffer through in a lifetime, and I’m still single. Which means that with each new man it’s once more into the breach, dear friends, once more.

After too much heartbreak, too much let down, too many guys who let me pick up the check and then tried to slobber on me, too many promised phone calls that never materialized, too many dudes who said they just weren’t ready for a girlfriend, and on and on, it sometime seems nearly impossible to believe that I might still meet The One.

But I refuse to accept defeat! And that means staying open to the possibility that, just like Fievel, somewhere out there, someone’s saying a prayer, then we’ll find one another, in that big somewhere out there, and, in the meantime, I have to cling to the slowly shriveling kernel of my heart that believes in romance.

Is your guy too good to be true? Maybe. Maybe not. There’s only one way to find out and that’s to ride this relationship out to the end, be it two weeks or ’til death do you part. The surefire way to kill it now is to smother the smoldering fire with your jaded insecurity. You’re in the first flush of romance now and that’s the most fun part! Kick back, relax and enjoy the awesomeness you’re been presented with. If it turns out to be too good to be true, at least you enjoyed it in the moment.


*Feel free to email us with any dating, relationship, love and sex questions you may have for Sasha.

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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