If You're An Optimist Dating A Pessimist, Here's What You Should Know

Look on the bright side!

Relationship Advice For Dating An Optimistic Or Pessimistic Person When You're The Opposite Radu Florin via Unsplash

By Laura Herndon

You’re a starry-eyed optimist with a half-full wine glass. They’re a gloomy pessimist who believes that wine tasting is a classist construct that damages the environment.

But despite your differences, you fall in love with them! What happens when the silver lining meets doomsday, though? 

RELATED: Can Optimistic Or Pessimistic Thinking Kill Relationships?


Fear not! It’s totally possible for an optimist and a pessimist to enjoy a beautiful romance — as long as both individuals are willing to be a little flexible.

If you’re an optimist dating a pessimist...

As an optimist, you enjoy looking on the bright side. While you experience setbacks, you simply choose not to let your struggles get the best of you.

In a relationship, this means that you’re immediately at your date’s doorstep with a picnic basket and a set of jumper cables when car trouble prevents them from making it to dinner.

When you met Prince or Princess Charming, their bright smile and cynicism about plastic straws swept you off your feet. Now, you find yourself unable to maintain your sunny disposition because they constantly focus on the gloom and doom! So, what can you do?


First and foremost, consider the motivation behind your partner’s pessimistic disposition. Do they struggle with depression or other health issues? Did their childhood negatively impact their life? Does their empathy push them to care too much about every little thing?

Once you understand what drives your significant other’s negativity, you can more easily validate their feelings with your own pragmatic outlook.

Your partner will appreciate your willingness to get on their level, and you’ll also feel more like your usual self.

RELATED: Why Pessimists Have Longer, More Satisfying Marriages, According To Science

If you’re a pessimist dating an optimist...

Like an optimist, you have your own take on life, even though yours is a little darker.


Instead of making lemonade out of lemons, you typically think of the worst-case scenario for everything — including relationships. If your date says that their car didn’t start, it’s clear that’s an excuse and they found someone better. 

But now, you’ve met that special someone who always makes lemonade out of lemons. Still, their constant flow of positivity is a bit much for you. After all, you’re not pessimistic, you’re realistic, right? 

Instead of assuming that our partner is just high on life, take a moment to understand why their eggs are always sunny-side up. Are they simply the helpful type? Do they ignore the world’s problems and spout eternal optimism? Or is all of their positivity just a façade?

RELATED: 13 Truths About Loving An Eternal Optimist (As Written By One)


If your partner simply loves hopeful outlooks, but willingly entertains other perspectives, then bask in their glow!

However, if your significant other uses their optimism to mask deeper issues, you should sit down and talk to them. Try starting the conversation with something like, “I love your positivity, but let’s work on a way to help you tackle your struggles. I know I feel better when I have a plan, and I think you might, too.”

As a former pessimist who graduated to “realist with a dose of optimism,” I can attest that love between an optimist and a pessimist can, in fact, work out in the end!


But (pessimists love a but), you need to be aware of your circumstances. It’s alright to be a bit glum now and then look for the best in every situation.

Whether you’re Eeyore or Tigger doesn't matter — not as long as you’re willing to love your polar-opposite partner exactly the way they are. 

RELATED: Pessimism Could Be Killing You — Here’s How To Crank Up The Sunshine

Laura Herndon is a writer who focuses on relationships, dating, and love. For more of her dating content, visit her author profile on Unwritten.