How to Use Failed Dates as Learning Experiences: 5 Lessons to Transform Your Romantic Mindset

It seemed like the perfect match — until it wasn’t.

Stacey and Rick were both professional writers, living abroad in Japan. They were both vegetarian, attractive, and witty when texting. When they connected on a dating app, she was excited to take him up on an invitation to sip sake in a hidden, upstairs bar that only locals (and he) knew about.

The date was going smoothly enough until about 30 minutes in when Stacey realized something. Rick hadn’t stopped talking about himself. He hadn’t asked her one question. As he was rambling on about the book he was working on, she found her attention drifting to all-too-common questions:

“Why is it so hard to find someone who’s worth my time and energy? Why must I have to endure so many bad dates to find a person who ignites sparks in my heart? When will dates stop feeling like one failure after another?”

It’s true: You have to break a lot of eggs to make an omelet — or in Stacey’s case, listen to selfish blathering for hours before finding someone who cares about her. For some singles, a seemingly endless stream of bad dates and even failed relationships can cause them to lose hope for love completely.

The key to ending this pattern of dating disasters is to focus on the lesson. When failed dates are learning experiences, it’s possible to transform a nightmare into the stuff that future dreams are made of.

But how can you do that, exactly? Let’s unpack the process of growing from hard life lessons like failed dating experiences. 

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Why Do We Date, Anyway?

When it seems like everyone around you is in a happy partnership, it can feel pretty lonely. You may start to doubt yourself and your self-worth. It’s easy to wonder what you’re doing wrong or where all the “good ones” can be found.

Dating is simply the hopeful act of looking for companionship, love, and someone to experience life with.

Rarely is it a one-and-done — you may have heard of people who go on one date and instantly find the love of their lives. Those are the exceptions, not the norm. Much more often, singles need to meet and get to know several people first. Dating experiences — even those that lead to relationships that last months or even years — can result in all kinds of rough emotions, especially when those long-term and short-term relationships don’t work out.

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Lesson #1: Honor Your Feelings

The most important of all dating lessons points back to yourself — you need to be able to feel and honor your emotions as they arise. This is important for your own emotional and mental health as well as for your future partner. The more you can identify and express how you’re feeling, the easier it will be to be honest and connect with someone else.

For example, Stacey finished that date feeling unheard, unworthy, and uninteresting. She felt hurt that Rick didn’t seem to care about her at all, and she was scared that she was never going to find someone who made her feel special.

When learning from failed dates, take stock of how you feel. Ask yourself:

• Does this date bring out the best in me?
• Do I feel comfortable in my own skin around this person?
• Am I being my authentic self?

Never compromise yourself or your personality to please your date, no matter how attracted you are to them. If your gut is telling you that something isn’t right, listen! You don’t need to overanalyze a strange feeling. There’s a reason you feel off. Honor yourself.

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Lesson #2: Remember Your Worth

Failed dates aren’t necessarily an indication that we need to change something. They are a great way to learn about what we need in a partner and what we don’t find desirable. Bad dates also give us perspective to know when someone does treat us in the way we deserve.

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No matter how many duds fill up your social calendar, you should never lower your standards just to make a relationship work. For example, if you expect someone to show up on time and your date is continually late, don’t brush it off. Tell them that it bothers you that they made you wait. If they’re more than 10 minutes late for the next date, leave and move on.

Stand up for what you believe is important. Always remember that you’re worth being treated with respect and kindness, no matter your past or your problems. Never accept less from potential partners.

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Lesson #3: Don’t Take a Bad Date Personally

Sure, if you’re the one doing all the talking and not asking any questions — like Rick — it’s a good idea to do some self-reflection (more on that in a minute). But otherwise, don’t presume that you did something wrong. You can’t force chemistry.

Compatibility isn’t a simple task, and it’s necessary if you want to have a fulfilling, long-term relationship. You must dovetail well with another person in a variety of ways such as: intellectually, emotionally, spiritually, and so on.

If any of these compatibility requirements are missing, it doesn’t mean that one person is “bad” or “wrong.” It just means it isn’t a good match. In life, awkward experiences are sometimes unavoidable. Staying positive and learning from a bad date can lead to better dates in the future. 

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Lesson #4: Learn Gratitude from Failure

After yet another bad date, it’s easy to feel overwhelmed with failure. When things don’t work out as we planned, it can be hard to accept. But failure is an opportunity for us to learn about ourselves and grow.

Gratitude is a powerful practice after a disappointing date. Aren’t you happy that you can feel and acknowledge those emotions after being around the wrong person? The more you can honestly appraise your feelings, the less time and energy you’ll waste on people who aren’t meant for you.

Some say there is no failure, only life lessons. When a date ends poorly, in effect you’ve:

• Built resiliency
• Gained perspective into what success could look like and feel like
• Helped yourself discover ways to approach the next situation with a better outlook
• Recognized what didn’t work so you can avoid that in the future

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Lesson #5: Focus on Self-Reflection

Never solely blame yourself for a dynamic that happens between two people. Unless you do something that’s really crazy, you aren’t the one who can make or break a date. Look at Stacey and Rick: somewhere, there’s a woman who will be enamored by Rick’s stories and want to hear more. Just because it wasn’t Stacey didn’t make either of them necessarily wrong.

Still, it’s worth investigating whether there is anything that you can do to improve your dating experiences. After a bad date, it’s a good idea to spend time understanding what went wrong to see if it’s something that you can fix. Keep in mind, sometimes there’s nothing at all you could have done differently to produce different results.

Try a journaling exercise. Set a timer for five minutes and commit to writing constantly the entire time. Think back on the date to see what worked and what didn’t. Write about what lessons you could learn and implement for a better date with someone else in the future. When the timer’s up, be done with it. Don’t dwell on it.

Another great self-reflection exercise is to imagine your perfect date. What does a good date mean to you? List desirable traits you’re looking for in a future partner, and imagine what it would feel like to be around a person like this. This can help you identify whether the next date is what you want to happen — or if it’s just another refining experience.

Bonus Lesson: Stay Positive

There is no guidebook on how to date. Because everyone is their own person, what works for one person on a date could be a total dealbreaker for another. But if there’s any rule for dating, it’s this: keep the faith.

Bad dates are bound to happen as you’re searching for that special person. Even though these disappointments are a great way to learn, it’s not like you want them. The more optimistic you are, the more likely things will eventually work out. Good dates will come in time. You just have to believe it. 

Poor compatibility in the past with someone else is in no way an indication that in the future another person will also lack compatibility with you. Unless you have identified something personal from introspection that you can address, perhaps with therapy or coaching, bad dates are just a part of life.

Think about your life as a puzzle. You have work, family, friends, hobbies, and everything else that fills up your day. And, there’s that one piece that’s missing, and that’s a romantic partnership. Don’t try to force a misshapen piece into your puzzle. Dating is just searching for the right shape — the right person.

It might take a little longer than you’d like, but you’ll find that special someone who fits into your life perfectly. Who knows? It could be your very next date.