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6 Important Dating Lessons I Learned in My 30s

Updated: Oct 23, 2023

After a much-needed heart sabbatical and some hefty personal work completed on my healing journey over the past few years, I found happiness, peace, strength, faith, and my glow. By 2021, I also dipped my toe in the dating pool. I'll start by saying that the dating scene is not for the faint of heart. And if you've been in the mix, you already know this to be true. While it can be fun and exciting if you approach it correctly, you can also easily find yourself on all types of roller coaster rides. I quickly discovered that it's kind of like a carnival--full of disappointments, smoke and mirrors, self-discoveries, and a little bit of crazy. But let's focus on discussing the lessons and the blessings I've gained from my short stint in dating post-divorce.

Here are 6 crucial dating lessons I've learned after reentering the dating world in my 30s.

If you're unhappy by yourself, you'll never be satisfied in a relationship/dating.

This one might feel cliche, but man, is it true. At the end of the day, you have to spend the rest of your life with YOU, so anyone else should add to your joy, not be the source of it. They must be the whipped cream and cherry, not the entire milkshake. Many people date in hopes of secretly fulfilling all of their desires and needs when in actuality, there's some necessary self-work and healing that needs to happen. Don't get me wrong, there's nothing wrong with desiring a relationship (Psalm 37:4) and dating with intentionality. However, it's vital that acquiring a relationship doesn't become an idol pursuit. You must genuinely be rooted and secure in yourself, so you don't rely entirely on someone else to dictate your happiness.

Can't be your true self? The connection ain't it.

Let's keep it real. Who wants to continuously walk on eggshells or operate as a watered-down, hollow version of themselves? A good, solid connection and relationship will create space to enhance who you are and help you improve or level up. It goes without saying, but I'll do it anyway. Being true to yourself is specifically related to your personality, interests, values, etc., not areas of improvement (that's another story). If you have to wear a mask or try to portray something you're not for love and acceptance, it's a wrap.

Maintaining individuality is important.

You're not someone's "other half." Yeah, I said it. You're a whole d*mn pizza by yourself. It can be easy to become enmeshed in the thrill of getting to know someone and spending every waking moment together to feel that rush and connection. But in reality, you want to date someone with a healthy lifestyle. This means he or she is connected to family, friends, a career, and hobbies/interests outside of you. Throughout any life stage, you must have "me time" and choose a partner that can help foster that while maintaining a romantic connection. Too much, too fast, too soon is usually ripe with infatuation and codependency. Hard pass.

No one is perfect, and that's okay.

Look, even the woman or man "of your dreams" will have quirks that get on your nerves occasionally. If you are single, you likely have "a list." I hate to break it to you, but the person for you may not completely check on said list. I've lived long enough to know that love isn't a fairytale. While it can have its moments, real love ultimately takes work, and the goal is to find a partner willing to roll up their sleeves for the long haul. Sometimes in dating, we set unrealistic expectations or create imaginary personas in our heads only to be set up for disappointment. You also have to clearly distinguish your preferences vs. non-negotiables. Remember that beauty fades and people experience various seasons in life, so what you see right now might not always be what you get. Date someone with the character, a strong moral compass, and the capacity to ride the wave of life with you.

Expectations are a buzzkill.

As a woman in her mid-30s, I get it. The tick-tock on the clock is loud sometimes. However, if you find yourself constantly scrutinizing every little thing in your head, it's pretty hard to actually enjoy the experience of getting to know someone new. When you live in the moment, and you're not freaking out about the timeline of what's "next," you'll be surprised how people naturally weed themselves out of the running. Placing expectations on people has a strong likelihood of ending in disappointment. If you date from a grounded and secure place (with standards in tow), you can enjoy things for what they are.

If someone is interested in you, you'll know. If you have to ask, you already have your answer.

So many people take ownership of being poor communicators, which I think is weird AF. But let me be clear, it's not the lack of communication skills, but why are they out here dating before doing the work? While it may be true that some people struggle in this area, it's not your job to "fix" anyone. All that said, if they can't talk, time to walk! Some women especially have a bad habit of getting their emotions tangled up in mixed signals and often find themselves performing for attention and validation. If someone's words and actions are inconsistent and don't align, it's a clear signal they aren't sure about you. The person who wants you and has clear intentions will be sure to make it known to you one way or another. In a nutshell, spend your precious time dating someone who cares enough to prioritize dating you.


Dating ultimately helped me learn so much about myself, needs vs. wants, and navigating relationships in general. Not all is lost when it comes to dating in your 30s. Despite societal pressures, there's no timeline for finding "your person." It will work out if it's meant to work out.

Happy dating!

And That's Just Ashley Blog

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