How To Date Confidently As An Overthinker

A first date can be pretty nerve-wracking.

Especially if social interaction is not your strong suit or if you struggle with overthinking and you always end up overanalyzing every part of the date. 

That’s why it’s SO important to have a game plan to help you put your best foot forward and show up as your most badass, confident self on that date!

Now, despite the title of this post, this article is actually going to be divided into 3 parts to cover what I consider to be the 3 crucial stages of the first date:

Before the date which includes getting physically (and mentally) ready for the date.

During the date which includes how to actually enjoy and get the most out of the date as it’s happening.

After the date which includes how to not go down a spiral of overthinking and worrying when the date is over.

Let’s dive in!

Before

Pick a badass outfit

In order to show up as your most confident self, you need to look your best. Whatever that means for you.

If there’s a certain hairstyle that you know you look amazing in, wear your hair that way. 

If there’s a pair of jeans that perfectly accentuates your figure, why not throw them on?

Personally, I love to wear medium-sized ear hoops. I think they work really well with my face shape and I look super cute with them! So in this scenario, I would def add a pair of hoops to my outfit.

You don’t need to get extremely dolled up if that’s not your style. But just find the item of clothing or accessory that you think looks amazing on you and you feel great in and wear it and rock it!

When you feel confident thanks to your outfit, you will radiate that confidence and everyone around will definitely take note!

Recite affirmations

I am a HUGE HUUUUGE fan of positive affirmations. I can’t say enough good things about them.

Before a first date, it’s crucial that you get yourself in a good headspace so you can exude fun and positive energy on the date itself.

Here are some examples of affirmations you can use but of course you can come up with your own:

  • I’m determined to have fun on this date.
  • I’m excited for the opportunity to connect with another human being.
  • I am beautiful inside and out.
  • I’m worthy.

This last one is special because there were many times in the past when I didn’t feel worthy or deserving whenever people showed interest in me and asked me out on dates. That’s why now as I continue my self-love journey, I always make sure to remind myself of that.

During

Take the focus away from yourself

When we go on dates, sometimes we worry so much about impressing the other person that we basically sabotage the whole thing from the start.

We take up most of the conversation to tell them as many interesting things about us as possible.

We fixate on what they must be thinking of us the whole time.

But ask yourself this: do YOU like them?

Take the focus away from yourself, chill out and take the time to get to know the person to see if you’re actually a good match.

Ask them questions, learn what they like and don’t like, find out if you have things in common. 

And don’t be afraid to be vulnerable and share a few things about yourself. If they respond well, that’s a good sign. If they don’t, there’s no need to take it personally. It just means you don’t see eye to eye on certain things. Which brings me to my next point…

Have fun with it (regardless of what happens!)

Regardless of what happens, just have fun with it. This date doesn’t have to be such a stressful experience.

Sometimes, we focus so much on the outcome of a date and we think way ahead and start planning our wedding to this person that we forget to be present and actually properly get to know them.

Whether or not you guys click and become a thing, there’s no reason why you can’t have a fun date. If you need some ideas for interesting dates that are not just some boring dinner, check out my article on stress-free first date ideas for socially awkward peeps here!

After

Distract yourself with other life stuff IMMEDIATELY so you don’t overthink

Back when I used to care so much about the outcome of first dates (especially if I really liked the person), immediately after, I would go into a spiral of:

  • This was fun. I wonder when he’ll text!
  • Why did I say this embarrassing thing earlier?!! He’ll think I’m a big weirdo!

Fun times!

It’s okay to think about the date a little and be excited about it but don’t ruminate about it. That’s why if you know you’re prone to this, get yourself busy IMMEDIATELY after!

If you have an assignment you’ve been procrastinating on, start it.

Make plans with friends ASAP so you have something to look forward to.

Leave your phone aside and catch up on your favorite TV show.

ANYTHING to get your mind off it. Desperate times call for desperate measures sometimes!

Accept that it may not work out the way you want

Not all dates have the happy endings that we’d like. And that’s okay!

It doesn’t matter if this happened already multiple times before with guys you really liked and you don’t want to go through the same hurt or embarrassment that comes with being rejected or him no longer texting back. Side note: Sabrina Zohar gives great advice on texting anxiety on her podcast, “Do The Work“. You should definitely check it out.

OR! Maybe you’re the one who rejects him. But whether or not you’re on the receiving it, it sucks either way.

However, it doesn’t have to be the end between you and this person. I can personally attest to the fact that even though a romantic connection may not develop with someone, you can actually become great friends with them instead.

I used to be so devastated if it didn’t work out, especially if I really liked the person. But these days, I’m learning to find peace with whatever the outcome ends up being. I choose to focus on abundance and remind myself that the right person is out there for me and we won’t miss each other when the time comes. 

(If you couldn’t tell, I’m a huge romantic lol).

So remember, if it doesn’t work out the way you wanted, it’s okay. You’ll survive. Repeat this to yourself 50 times if you need to.

Moral of the story: rejection (of any sort) is redirection. Learn to get comfortable with it and become confident in yourself and the fact that there is still better for you out there!

Ready to date with more confidence now?