By Carlos Kotkin

There’s no way around it.  First kisses are usually pretty awkward, and yet they’re almost always memorable.  Even celebrities commit their first kiss experiences to memory.  Recently, a group of celebrities including Tom Green shared recollections of their first smooch with People.  For instance, Jerry O’Connell was stunned when his first kiss took a French turn.  Vince Gill’s first lip lock involved intense face slamming that kept him from breathing.  James Van Der Beek’s extremely romantic first smooch took place in a … handicapped bathroom?  A handicapped bathroom?  Seriously?

Even after you’ve gotten the hang of it, a kiss at the end of a first date can sometimes be just as awkward.  These situations bring you back to your teenage years when you were kissing your teddy bear for practice.  To top it off, for guys, making the first move is often a nerve-wracking experience … and as they say, timing is everything.  Here are some things to consider:

A Concrete “No”

It’s no secret that dating can be an awful experience every now and then (or nine times out of ten).  The worst part of a first outing is the potential for an awkward goodbye at the end of it.  Indeed, I’ve experienced my fair share of goodbyes.  Sometimes it’s crystal clear when a woman isn’t interested in a first kiss … or a second date, for that matter.  At the end of one date, I received a firm business-like handshake along with a “Good luck to you,” before she power-walked in heels across the parking structure to her car.  In that case, I knew leaning in for a kiss wasn’t a great idea.

Related: Five Conversations to Avoid on the First Date

A Strong “Yes”

Other times, women I’ve gone out with have miraculously been attracted to me.  In one case, at the end of a date, a young lady asked me point blank, “Are you going to kiss me or what?”  This was a strong indication she wanted me to, um, kiss her.

Related: Five Reasons Why Opposites Attract

No Man’s Land

But then there’s that middle ground — that neutral date when you’re out with someone and you feel like things could go either way.  It’s the no-man’s land of dating.  Unfortunately, this is where I’ve ended up most of the time.  I’ve been in situations where I’ve thought, “This person either can’t stand me or is head over heels.”  I’m not embarrassed to admit I’ve been on a date at the movies and as the movie was ending, I’ve thought, “Oh, no.  It’s over.  We’re going to say our goodbyes pretty soon.  Oh no…”  Ladies, while in no-man’s land, your date will search for the slightest clue that you’re more than friends.  The gentlest touch from you, laughing at our stupidest jokes or a twinkle in your eye are all strong indicators.  (By the way, it’s totally possible to see twinkles.)  The bottom line is, things like that give a guy hope.

While I can’t point out which specific clue will lead a guy to lean in, I can emphasize what not to do.  I was on a dinner date once that lasted for hours.  We ended up in my apartment, where she sat on the couch, giggling at my yearbook photos.  When I leaned in, she moved away in surprise, saying, “I’m not interested in that.  Sorry.”  I apologized profusely, declaring it was my bad.  Even though the atmosphere was incredibly awkward afterward (I thought), she stayed for another hour as if I had never made a move.  We talked about Hawaii, and she finally left.  When she did, I had a newfound admiration for the woman who shook my hand and power-walked away in heels.

Carlos Kotkin is the author of PLEASE GOD LET IT BE HERPES: A Heartfelt Quest for Love and Companionship.  He is a ten-time Moth StorySLAM winner, including two-time winner of the coveted GrandSLAM, and has been featured on NPR’s The Moth Radio Hour, KCRW’s UnFictional, and the popular podcast RISK! He lives in Los Angeles.  For more on Carlos, visit his website at www.carloskotkin.com.