Why Worrying “Is He Into Me” is a Guarantee That He Won’t Be

It’s pathetic that at 60+ I can still find myself acting like a wounded little high school girl.

Thankfully, that foolishness doesn’t come up too often these days.

I don’t get all freaked out about men anymore. I’m secure in knowing that my husband loves me…almost all of the time.

Girlfriends, though, are still super important to me. So these days I find myself in regression mode is when I start feeling a chick crush coming on.

And off I go…trying to figure out if she’s also into me.

She laughed at what I said…but was it sincere? She seems interested in I mentioned it would be fun to have lunch sometime, but she didn’t pull out her phone to choose a date. Did she mean it?  In a flash, I can be back in the 9th grade, grieving over my (perceived) lack of popularity, and ready to give up on trying to make new friends… forever.

woman crying does he like me

I have spent tens of thousands of dollars and numerous decades in coaching and therapy learning how to overcome my compulsion to gain the approval of strangers. Because here’s the thing:

As soon as I get in my head and start going down the does-she-dig me rabbit-hole…the real me virtually disappears.

I act bashful (which I most definitely am not).

Sometimes I over-compensate and act like some look-at-me cocky broad. (Which, okay…once in a while I really am.)

I’ll hold back compliments, lest I tip my hand to someone who doesn’t like me back. (Yah, as I write that I realize I sound like a 12-year-old. Charming, isn’t it?)

And my favorite reaction of all: I “protect myself” by looking for reasons not to like her. And, lo and behold, I can always find a reason. Whew! Emotional catastrophe averted!

Intellectually I know that jumping to the “I bet she doesn’t like me” crap is all in my head. After all, I’m quite a likable gal. This is a base fear of rejection stemming from being quasi-raised by a narcissistic mother. (Every  one of my unattractive qualities is her fault, of course.)

Can you relate to this self-sabotaging behavior at all? Maybe not with women…but can you see yourself in any of this when you’re meeting single men?

If so, you know that it is sometimes hard to ignore these icky insecure feelings, whether you’re 18 or 68.

Feeling like you’re going to be rejected sucks. Here are two ways to stop the madness!

Over the years this has caused me real pain. And I bet a lot of potentially great relationships. But there’s a big difference between when it happened in high school and when it happens now.

Now I have skills to help me move through the knee-jerk nonsense so I don’t devolve into the reactions that screw up any chance I have of making a connection.

As soon as I realize I’m in the “does she like me” mode, I have a quick conversation with myself. It usually goes something like this:

Stop! You’re acting like a high school girl. She has shown no clear sign that she doesn’t like you. It’s old stuff and all in your head. Just be yourself, because you’re terrific. There’s no reason they won’t like you. And hey, if they don’t, then you’re just not meant to be friends! 

I try to drop back into reality and be kind to myself. I try to remember that obsessing about what she thinks can screw up any chance I have of opening the door to a fun and interesting friendship.

It almost always works.

Having that grownup self-talk is your Tip #1. 

These days my angst is all about chicks. But it was definitely a pattern for me as I started dating and looking for love.

When I’d meet any kind of available man, within a few short minutes off I’d go!

Is he into me? Does he seem to notice or care how fat my thighs are? Does he think I’m a loser because I’m so old and not married? Is he acting like he’s going to ask me out (again)?

Arrrghh! Exhausting!

Looking back, I’m positive that this affected how I acted when I met men, and it probably cost me some good dating action. But once I learned the “be real and be nice to yourself” self-talk tool, it helped me a lot when I entered the world of mature dating.

With the volume of my internal chatter lowered, I was more present and able to be more of my delightful, fascinating self. More men were into me.

But…that’s not all I have for you! Here is the second thing that put the icing on my grownup dating cake:

Tip #2 will rock your world: First decide whether you like him.

Think about that. Remember the chat I have with myself: if she doesn’t feel the same connection with you, then you’re just not meant to be friends!

Welp…it’s the same with men!

Think about it. Do you ever start with “do I like him?” Is this a man you feel good being with? Does he seem like someone you want to get to know better? Does he show any potential to have the qualities you need in order to be happy with this dude?


So often I never even got to that question because I was so wrapped up in whether he liked me. Do I like him? Once I learned to ask this first, it turned out I didn’t even need to have that whole other conversation with myself. Because if the answer was “no,” the rest didn’t matter.

It took me a lot of time and money to learn this. It’s pretty simple, isn’t it? It honestly changed the way I looked at men and, surprisingly, it changed the way I thought about myself. Asking and answering this first kept me from wasting time and energy wondering if I was liked by someone I didn’t even like. But more importantly, it forced me to think of myself first. What do I want? Does this man seem worthy of me? These were questions I hadn’t been asking myself.

Try it. Next time you meet a new, available man, ask yourself this: Do I like him?

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