The Lower Brain: Too Shy

When I was in high school I struggled with being too shy to talk to women. Even when I had girlfriends, I was scared to make the first move, hold their hand, or show them affection in public for fear of overwhelming them or being rejected.

 In my 20’s I overcompensated and only years later learned that I could be all too available and very overbearing. Now in my 30’s I’m struggling to find the balance. I’ve learned from my mistakes of, “I’M FREE! I CAN HANG OUT WITH YOU TONIGHT!” or when she’s most likely just venting, “I CAN FIX IT!” but I know I gotta have some sort of communication with the person I’m interested in. The lady I like now is fresh out of a relationship and not looking for something serious, but I am looking for something serious. Any advice on finding the right balance?

 -Anonymous guy that’s really good at writing quick and to the point questions, would you believe I’m single?

(photo by Getty Images)


Naturally shy people are the best! Much like the pyramids at Giza or really big hair, shy people are full of secrets. They’re often funny, sweet, fascinating, goofy, talented…the list goes on. And wow, you are really doing the work by looking at yourself and taking stock of your history and present. It sounds to me like you had some intense social anxiety when you were younger, and have spent your adult life thus far figuring out what works and what doesn’t. Trial and error, right? As long as you proceed with good intent and tell the truth (in a polite way), you’re good to go. And it sounds like you’ve done that.

But let’s talk about seriously dating this newly single gal. Take it from somebody who has been in your Jordans and in her Louboutins (or maybe you guys just wear flip flops?): if she ain’t ready, you can’t make her ready. And I don’t get the vibe you want to force the emotions or anything like that. I just want to remind you to take care of yourself first. Also, you may find some answers and some comfort in books. Some of them may not totally fit the bill, but they may still have good insights.

For example, I’ve been reading a pretty good book called  Addiction to Love: Overcoming Obsession and Dependency in Relationships by Susan Peabody. I’ve never been scary-obsessed with a person, but that’s the extreme end of the spectrum of unhealthy romantic fixation. I’ve still gotten caught up in drama or even helped create some. I used to get into relationships all the time with folks who weren’t really ready to be committed. It was a kind of challenge for me – can I “make” them love me? Can I “make” them want to be with me?

The truth, of course, is that you can’t “make” anybody do anything unless you’re threatening them with violence as the alternative. And you and I don’t do that, nor will we ever do that, right? Right. So. It’s truly a fool’s errand to try and lock somebody down as your person when they’re just focused on figuring out how to be their own person.

Anyway, my point is this: instead of putting your energies into pursuing this gal, I think you ought to let her know you’re interested but no pressure, you know she’s taking care of herself and you respect that. Tell her you’re doing your thing, living your life, and if she’d like to go out sometime, cool. If not, that’s cool too. Then actually do your thing and live your life.  You might want to check out some books for natural introverts and/or shy people, because while you’ve learned to be more outgoing and social, you still may need alone time in order to recharge.

My friend Emma (she’s a big YouTube star who does ASMR videos as WhispersRed) recommended a book called Quiet: The Power of Introverts In A World That Can’t Stop Talking by Susan Cain. I haven’t read it, but it’s a bestseller and a lot of people love it. I have a feeling you might discover some insights about yourself in that book.

Also, make sure your life is full in other ways so that your sole focus doesn’t become romantic fulfillment. I retired from codependent romance a couple of years ago (I had a good run, by which I mean a long and often bad run). I’ve dated around but haven’t gotten into anything serious. As a result, I’ve had more time to write, to visit my family, to hang out with friends, to travel, and to re-teach myself to cook and bake.  I haven’t been celibate or isolated – in fact, I’ve been more engaged in the world than I was back when I was so caught up with whatever boyfriend (or occasional girlfriend) I had. I think I’m a better person now. Plus, I finally learned what the designated hitter rule is. This joy and more can be yours if you make sure to look after yourself first.

In my opinion, there’s nothing more attractive to somebody else than a person who doesn’t need them in order to be happy. I figured this out a couple years ago and decided to become the kind of person I’d want to date. I’m not there yet, but maybe it’s not about the goal – it’s about the experience of trying. And you’ve proven yourself more than able to grow, change, pivot, evolve. You’re on the right track. Somebody is going to be very lucky to have you one day, and you’re going to be very lucky to have her – but also, you’ll know you earned it because you did the work.