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5 Reasons You Should Go On More First Dates

5 Reasons You Should Go On More First Dates
I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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I always thought I’d know when I met “the one.” He’d walk into the room and my heart would jump. I thought he’d arrive with a note attached,  “Dear Stephanie, this is your husband. Love, God.”

But you know what the crazy thing is? I didn’t know. I didn’t know when I met him. I didn’t know when we became friends. I didn’t even know after our first date. I went home after our super casual first date — a chilly walk to the lake with hot chocolate — and thought, “That’s interesting. Carl is different than I thought.”

Carl surprised me, made me want to get to know him better. But I still didn’t know.

The other day I was chatting with some dear friends about how we overthink dating. We look for signs, for an arrow that reads “Over here! If you go on a date with this guy, you’ll get married!” So we put up walls and create strict lists about exactly what a guy needs to look like, listen to, or laugh about to get a date with us. And sometimes even when a guy meets our criteria, we still say no because we’re not 100% sure he could become our husband. My dear friend Kait admitted her list used to make it impossible to find a date.

“My expectations were so high,” she told me one time. “My list made me blind to the actual good men out there.”

Putting ourselves out there is scary and hard, I know, but I think we often put too much pressure on ourselves to “just know” way too early. Can we make dating simple again? It’s just getting to know somebody, after all. Maybe your story will unfold differently than you expect — I know mine did! But we’ll never know unless we give dating a try.

So friends, in the spirit of faith, hope, and giving yourself and your future husband a chance, here are five reasons we should be going on more first dates.

1. Dating can be fun!

First dates are a great time to try something or someplace new. Want to check out that cool new restaurant? Feeling nostalgic for a round of mini golf? These are great settings for a first date. Though dating feels a little uncomfortable in the beginning, you might end up with a new favorite hangout, hobby, or interest in a topic you learned about on a date.

When you think of dating as simply a chance to meet new people and try something new, the pressure melts away. It really can be fun instead of stressful.

2. Dating is a chance to get to know more people.

First dates are a total roll of the dice. But how will we know if a guy is our type or not unless we spend time with him? My friend Carly is all for casting a wide net. This doesn’t mean she said yes to every single guy, but it does mean she eased up on her list of requirements. She gave guys a shot.

Her advice: “Based on the information you have now, are you interested in knowing more about this person? If so, go on that first date.”

Friends, I just love this quote from former Google CEO Eric Schmidt. “Saying yes is how you get your first job and your next job, your spouse and even your kids. Saying yes means you will do something new, meet someone new and make a difference.”

He might not have been talking specifically about dates, but it certainly applies! You’re not saying yes to a marriage proposal or even a relationship by saying yes to a first date. It’s one conversation. One meal. One evening to get to know someone new. But you never know what could happen unless you say yes.

3. Dating with intention: You never know until you try.

Should we only go on dates with men we could see ourselves marrying? It’s a great concept in theory, but how are we supposed to know? This logic suggests we need to know if a guy is marriage material before we even know his coffee order! That’s a tall order (like my Starbucks joke?). The truth is that we can only make decisions — about first dates, second dates, or relationships — with the information we have right now. A first date doesn’t need to be (and shouldn’t be) high pressure. It doesn’t mean committing to weeks or months of dating.

I say this all the time to the women in my course, Love Your Single Life, but remember that our batting averages will be low. They’re supposed to be. Dating is a process of elimination, after all. We might go on 50 first dates, 10 second dates, and have only a handful of relationships. When Carly moved to Nashville, she explored the city by going on 17 first dates in 17 days. How many of those 17 first dates turned into second dates? Not many. But after all those dates, one ended up being Carly’s husband! That’s a TERRIBLE batting average, but it’s supposed to be! We will meet a lot of guys in life before we find the one who is right for us, but you’ll never know if this person is your person until you get to know him.

4. Dating helps you narrow your must-have list

The more dates we go on, and the more people we meet, the more we start to uncover what we’re truly looking for in our forever relationship. When I first started dating after becoming a Christian, my only requirement was that he loved Jesus. And that’s not a bad starting place!

But as I dated more guys, I learned I was looking for a few other things too. After dating someone I could talk to about literally anything and everything, I realized — I want that! So it went on my must-have list. Then I dated someone who loved Jesus but didn’t love my career aspirations. That helped me realize support for my dreams was a non-negotiable for me. Each date taught me a little more about what I was (or wasn’t) looking for. And so it didn’t take long after meeting Carl to realize, “Oh my goodness, this guy really FITS me!”

5. Dating helps us become better communicators.

Going on dates and connecting with different people is practice for being in a relationship. Being in relationships is practice for marriage. So as you’re dating, know that these conversations, these dates (even the breakups!) are not a waste of time. Each connection, however short, is an opportunity for you to grow as a person. You become better at small talk, better at communicating your needs, better at clarifying your passions and beliefs. It’s a great chance to learn more about your communication style in relationships, helping each next one get better and better.

Friends, I hope this helped your hearts today. Remember, we’re SUPPOSED to have a low batting average! It really is okay to have a bad first date (or a string of them!) They’re not supposed to all be home-runs! It really is okay when a date turns into a friend instead of a boyfriend. It really is okay to say yes to a first date just because you’re curious. I’m so glad I didn’t say no to Carl just because he didn’t have a post-it on his forehead saying “Stephanie’s future husband.” Carly had the same experience with her husband, and she remembers how free she felt when she relaxed her expectations on dating and just let herself have fun!

Friends, if you’re still unsure about whether your heart is ready to jump into the dating world, I have a resource that can help. It’s a free 10-question quiz called “Are You Ready to Start Dating?”

If you think you might be ready to date, but your dating prospects are feeling a little thing these days, this new resource is for you!

And if you'd like to hear some of Carly’s super practical tips, like what to wear and what to order on a first date, listen to the rest of my Girls Night conversation with her! I’m so excited to share it with you!

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5 Reasons you should go on more first dates and why dating can be fun

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  1. I like how you mentioned how dating more can help you know what you’re looking for. Since I haven’t been on a date for months because of COVID, I want to get out there again and I feel rusty. I’ll have to find a good restaurant that I can take a nice girl to.

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