I Stopped Auditing My Dates and Started Enjoying Them: Four Steps to Enjoy Your Dates Again!

If you can build a career in Baltimore, Washington, DC, or anywhere in the surrounding Maryland and Northern Virginia orbit, you already know how to achieve! You know how to prepare, perform, read subtext, and anticipate five steps ahead. You know how to sit at a table and hold your own.

I brought that exact energy into dating.

And it backfired…every. single. time 

For years, I dated from a checklist mentality. I was analyzing, sorting, assessing, projecting. I could clock attachment patterns before the appetizers arrived. I was scanning for red flags before the drinks hit the table. And somehow, even with all that effort, I left dates feeling dissatisfied and, honestly, more discouraged than before.

Being a therapist made it worse! There is this subtle pressure that we are supposed to know better when it comes to relationships. So when I found myself overthinking texts or replaying conversations on the drive home, I layered self-judgment on top of it. Why am I like this? Shouldn’t I be better at this?

Exhausting does not even cover it. 

I have been on more first dates than I can count or even would like to admit that I’ve been on. Pretentious conversations over-priced oatmilk lattes. Walks around the harbor in the blazing summer heat. Quick drinks that turned into two-hour magical conversations. Dinners that should have just been apps. And many many calls/texts to my friends and therapy sessions with my therapist to process them all!

If I am being radically honest, I low-key treated many of these dates like discovery calls.

Zero out of ten. Do not recommend.

Here is what was often running through my mind, and I know it runs through yours, too.

• Is he emotionally available?

• What is his attachment style?

• Is he actually single?

• Are our birth charts compatible?

• How much does he lift at the gym?

• Is that a red flag or am I projecting?

• Is this my husband and I just do not know it yet???

Meanwhile, the man across from me is just trying to tell me about his adorable dog and enjoy the moment over herbal tea and a nice view.

At some point, I had to lovingly call myself out. While some of these questions are absolutely valid and need to be answered with clarity, some can wait and be answered with time.

I was approaching connection from fear instead of enjoyment. I was trying to outthink uncertainty instead of actually feeling into the experience. I trusted my intellect more than my nervous system.

And here is the humbling part. My nervous system had been giving me information the entire time. I just was not listening!

Dating from a regulated place required me to do something radical.

Enjoy myself first ☺️

Not secure the outcome. Not decide if he was the one. Not scan for long-term compatibility by minute 37.

Enjoy myself!

• Can I laugh with him?

• Do I feel relaxed in my body?

• Am I being warm and open or subtly interviewing him?

• What version of myself is alive while I'm with him?

• Is this man adding to my experience?

• And equally important, am I adding to his?

That shift changed everything!

In this region, especially, so many of us are high-functioning, deeply competent professionals. We know how to build careers. We know how to hold responsibility. But intimacy requires something softer. Less polished. Less strategic.

You cannot spreadsheet your way into chemistry. I have tried and failed every time 🙃.

When I started paying attention to my body instead of my mental checklist, dating became lighter. If my shoulders were up by my ears and my jaw was tight, that was data. If I felt calm, playful, curious, that was data too.

Here are four ways I now regulate and teach my clients to regulate when the overthinking starts creeping back in.

1. Notice when you are conducting an interview. If you are mentally scoring answers, pause. You are on a first date, not hiring a CFO. You do not need his five-year plan tonight. Let the conversation unfold. You are getting to know a whole human being. That takes time!

   
   

2. Check your body before your brain. Are you leaning in and smiling naturally or are you bracing. Your nervous system is intelligent. It knows before your mind builds a narrative. And the space between dates matters. One date per week allows clarity. Four dates in one week is flooding, not romantic, not cute.

   
   

3. Make enjoyment your first filter. Did I have fun? Did I feel like myself? If the answer is no, it does not matter how impressive he is on paper. Attraction cannot grow in tension. Can you enjoy each other’s company, even in silence? Pauses are not problems. They are space to breathe.

   
   

4. Stop trying to solve the future tonight. You do not need to know where this is going. You need to know how this feels right now. Regulation lives in the present. Anxiety lives in projection. Stay in the mini adventure of two people choosing to sit across from each other. It is actually kind of sweet 😄

I had to learn that I do not need to secure love to feel safe. I need to stay connected to myself while it unfolds.

So maybe the invitation for all of us dating in Baltimore, DC, and beyond is this.

What if this was not another arena to win?

What if you let yourself be a little less impressive and a little more alive?

When you date from a regulated nervous system, you do not grip. You do not chase clarity prematurely. You do not abandon your standards, but you also do not abandon your joy ✨

You sit across from someone. You breathe. You laugh.

And for now, that is enough 🫶🏽

If you feel like you need additional support with navigating the ever-flowing nuances of dating, reach out and schedule a free 15min consultation call. I'm happy to support you through this!