Dear Just The Tips,

I have started seeing someone great. He’s interesting, funny and mature but when it comes to kissing he just stuck his tongue out in my mouth and that was horrible and made me not want to kiss him ever again despite liking him.

My question is threefold:

  1. Should I bother telling him?
  2. If so, how?
  3. How can a 40-year-old not know how to kiss?

Love, Tonguetied in NYC

Dear Tonguetied,

You’ve laid out your question beautifully. Thus, I say to you:

  1. Maybe not verbally, but ultimately yes.
  2. That’s why I’m here!
  3. There are a million things most 40-year-olds are bad at. This guy just ended up being bad at one thing that’s particularly inconvenient for you.

Your predicament reminds me of my first kiss.

We were in a field somewhere in rural Massachusetts and snuck off from a game of Spin The Bottle. He had returned from summer camp with a haircut vaguely resembling Devon Sawa’s and an attitude like Billie Joe Armstrong. I had the attitude of Christina Ricci in Now and Then but with Gwen Stefani’s braces.

We shared a seat on the bus back from our 8th grade bonding trip during which I tried to make it clear that I liked him by:

  • maintaining as much eye contact as possible
  • talking about how awesome “Rage Against the Machine” and the genre of “Ska” music was.
  • saying how cool i thought his mom was.

At one point I uttered the words, “I’m a firm believer in second chances.” While it meant absolutely nothing coming from a 14-year-old, I seemed to strike him as cool enough to plant one on me a few weeks later. Or maybe I smelled good. Or he was just horny. Who knows.

The point is, it was terrible.

It was like his tongue was a fish that had just been caught had been thrown onto the deck that was my mouth. I choked. I laughed out loud. I thought to myself: “It can only get better.” It didn’t.

We “dated” for 8 months and never kissed again. Not once. I do not recommend you follow suit. I suggest you take your experience as an opportunity to be proactive. It sounds like you like this guy and it’s worth pursuing ways to teach a (40-year-old) dog some new tricks.

1. Figure out what made it so bad.

You say he just stuck his tongue in your mouth? Does that mean it’d be better if he moved his tongue around more or used less tongue? Make a specific mental note about what was lacking, then…

2. Give it another shot.

I stand by what I said at age 14: I am a firm believe in second chances. If you are dealing with a bad kisser, give it a little bit of time. People get weird. They may be drunk, lazy, or so in love with you that they don’t even realize what they’re doing to you with their mouths.

3. Get ready to improv.

Once you find yourself granting the bad kisser a second (or third or fourth or fifth) chance, use the first rule of improvisation: “yes AND” as opposed to NO but. See what you can do to work around or improve the situation. Can you maneuver around his tongue? Kiss his neck? Nudge his ear? Make another non verbal suggestion that’s more along the lines of what you like.

4. Make the environment around the kissing less brutal.

The goodbye kiss can bring an unexpected amount of performance anxiety. Don’t worry about the perfect moment and don’t impose that pressure on him.

5. Go Dancing.

Or find another activity that connects you with your body. You didn’t mention how he is in other embodied activities. Does it feel great when he touches you? Have you slept with him? I always say if somebody can dance, hug and fuck they’re worth keeping around. Proceed.

6. Evaluate how committed you are.

If you are committed it’s time to have a conversation about this explicitly. If you’re not, perhaps it’s time to say “bye Felicia.”

7. Propose an “experiment.”

You’ve experimented with making physical suggestions; now let’s move onto verbal ones. Say: “What if we just used our lips?” or “I want you to almost put your tongue in my mouth but then don’t.” Or even, “What if we have sex without kissing?”

8. Do a little R and D.

What does he say about past relationships and sexual experiences? We make assumptions about people’s sexual histories all the time based on their age or other factors and it’s not always fair to do so.

9. Bring Out Their Softer Side.

His style sounds rather aggressive. Discern, either physically or verbally, what his softer side might be like and then work from there. It’s a much different thing to kiss a person after you’ve shared something intimate about yourself with them.

If that doesn’t work then…

10. Bail.

Kissing shows a fundamental way of how you’re turned on. You don’t want to deny him that. Or deny yourself the pleasure of finding somebody who really “gets” how you kiss. Making your partner into a better kisser might become the focus of your relationship which is no good. Best to avert disaster.

Remember that kissing is an extension of the conversation. And we learn the arts of conversation and romance at different rates. Kissing requires a light attention, curiosity, and an ability to stay on topic, an openness to non-sequiturs and a willingness to go deep without coming off as invasive. It’s occasionally made better by drink but gets sloppy and offensive with too much. It’s possible to do in large groups but best when kept to private quarters where you can hear the other person, pay attention to their social cues and nuances and take a break for silence when necessary.

People often kiss the way they talk. If they don’t, they’ve been lying.

The things I didn’t mention to you about my first kiss were that I faked my interest in Rage Against the Machine, overlooked the fact that his eyes glazed over when I talked about the music I actually adored, and that trying to hold eye contact for that long was completely exhausting and uncomfortable! It’s no wonder we weren’t compatible.

We often only hear and see only what we want to when we think we are attracted to people. Next time, listen carefully.


Just the Tips is’s weekly advice column, with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at