If you’re like many introverts, you may have a tendency to overthink dating. After all, there are so many things to ruminate about in the search for love.

Some aspects of introvert dating that may get your brain spinning with indecision and worry include:

  • How to navigate dating apps
  • How to read confusing signals
  • Whether to make the first move
  • Whether to offer to pay
  • What to talk about
  • What to do on dates
  • How much to share
  • Whether to have “the talk” about where you stand…

All of the above are future-focused worries. You overthink hypotheticals. Introverts also do a lot of post mortem overthinking.

You might dissect a conversation with surgical precision, examining every sentence and facial expression. You wonder, “did I say the right thing?”, “Did I come off too aloof?”, “Did he notice the spinach stuck in my teeth?”

All the ruminating can be absolutely exhausting. This is a big problem for introverts who are already drained and overwhelmed by the whole dating process. Because here’s the thing…

Traditional dating, like many other social activities, wasn’t designed with introverts in mind. It often involves so many things that make introverts want to run for the hills: noisy bars, small talk, rushed intimacy.

Introvert dating during a pandemic

One gift from the pandemic is that it’s changed the way people date.

People are getting to know each other more slowly through messaging and video chats. Instead of going to bars for a first date, they’re going on walks.

Of course, there are challenges, too. Some people are losing hope. They worry that it’s impossible to meet Mr. or Mrs. Right under these circumstances.

So, they give up before they even try, which is another way that overthinking gets the better of introverts.

It allows us to make excuses for ourselves and not go for what we really want. Luckily, there are ways to move past all the overthinking, so that introverts date with confidence.

How Introverts Can Stop Overthinking Dating

Recognize why you overthink

The first step is to recognize that overthinking is a form of procrastination. It’s the ego digging in its heels against change.

You say, “I want a loving relationship, so I’m gonna try something different”, and the ego responds with an encyclopedia of reasons to stay stuck in fear.

Simply noticing the subconscious driver behind all the ruminating will help you move past it.

Stop meeting conditions

Overthinking causes introverts to fall into a pattern of “meeting conditions”.

This means that instead of taking the one (usually scary) action that will get you a date, you do a bunch of other things that seem important, but ultimately won’t get you anywhere.

For example, you tell yourself you have to get a new wardrobe, pay off debt, see a therapist, and lose 10 lbs if you want to find love.

While those things are all fine and good, they are not what will ultimately get you a date. The most direct route to getting a date is to ask someone on a date.

Accept that there will be discomfort

When I work with 1:1 dating coaching clients, the initial fear that often comes up is that they will have to do a lot of things that are uncomfortable.

They imagine that they’ll have to exhaust themselves by going to a bunch of Meetups, and putting themselves out there in very extroverted ways.

The truth is that if you want to break a pattern of loneliness and find love there absolutely WILL be discomfort involved. But not in the way that you might think.

The discomfort usually has to do with breaking a pattern that your ego sells as safety.

For example, if you normally hide and deny your attraction, you endure the discomfort of letting it be known. Instead of playing it cool, you open your heart.

As an introvert, you can date, flirt, and open up to love on your own terms—no extroversion required.

It helps to have some concrete, introvert-specific flirting and first date tips to curb the overthinking and date with confidence.

That’s why I put together my two free dating guides for introverted men and women, which you can download below.

First Date Checklist For Introverted Women
Flirting Guide For Introverted Men

Transform your love life on a deeper level

As an introvert, you probably know that flirting tips alone won’t work if you have subconscious blocks and patterns that push love away.

That’s why over the couple of years, I’ve been working with new, groundbreaking tools to shift painful patterns at a deep level.

These advanced methods have been creating rapid shifts in my own life and those of my clients. But I have to be honest. It is impossible to do this work on your own. Whether you lean on the guidance of family, friends, therapists, or online mentors who understand you, support is crucial.

If you’re ready to finally get out of a love rut and create massive shifts in your dating life and relationships, I’d love to be your guide!

I work one-on-one with a very select few introverts like you to help them get unstuck and open up to love. Spaces are limited, so if you’re interested in working with me closely, here’s what to do next:

  1. Fill out an application for a complimentary 30-minute Breakthrough Session. 
  2. Check your inbox for a response to your application within 48 hours.
  3. During the 30-minute session, we’ll get clear on where you are now and what might be holding you back. 

Along the way, I’ll share insights and steps to move forward. It’s a great way to see if we’re a fit for working together.



Michaela Chung