The Ultimate Guide to First Dates
Updated: Jun 25
Do you remember how when you were a kid, you’d meet another kid and be instant BFFs? I remember when I was in sixth or seventh grade, a girl in my class said, “Caitlin, I can’t believe it’s not butter!” And we were instant best friends for decades. I have no idea why she said that but it was funny and the rest is history.
Well, dating isn’t like that. You don’t go out with someone once and instantly have a relationship. In fact, you don’t go out with someone twice, or three times and have a meaningful relationship. You could do that, but you’d be getting into a relationship with someone you don’t know. In this modern dating world of fast-paced swiping, screwing, and ghosting, it’s important to take control of your dating life and slow things down. Relationships take time to develop—a lot of time—and trying to keep up with the fast pace of the online world is only going to keep you from finding the right partner.
Let’s talk about the first date. When I was single and first began my dating journey, I remember how excited I’d get after a good first date. I’d go home, hope the guy would text me, and tell all my friends about him. After just one date, he was a big deal to me. Whether or not this semi-stranger texted me was a big deal. And by around the third date, I was ready to commit. But, way too often, after about three to five dates, the man I’d been so excited about would either start pulling back or he would ghost me. And of course, I felt hurt again and again.
At the time, I didn’t realize that I felt rejected by men I hardly knew, and who didn’t mean much to me. The idea of them meant a lot to me. The idea of my future with this idealized man meant a lot to me. The actual man? Well, he was usually far from the one I'd imagined him to be, but I couldn't see that until much later.
There’s nothing wrong with being excited about someone you’ve met. But there is a difference between being excited about someone you met, and being excited about the idea of someone you met. And it's important to know the difference.
If you’re tired of going on a few dates, getting excited, and then ending up disappointed and starting from scratch, the following tips can help:
1. Know the difference between what you hope for and reality. No matter how good you feel after your first date, you don’t know the person. You may feel comfortable, you may be attracted, the conversation might flow easily, etc. You may even have hot sex on the first date—no shame if you do! But you still don’t know the person, and you certainly don’t know if they are a good match for you. You spent a few hours together, maybe a day if you were really into it. That’s not anywhere near enough time to know this person. If you’re super excited and into him, you’re probably into who you think he is (this is also known as a projection).
2. Approach the first date cautiously. There’s a lot of guidance out there telling you to be open, be yourself, be vulnerable, etc. But you should think of a first date the same way you think of a nice chat with a stranger during a bus ride. You’re probably not going to share your deepest wounds and go have sex with that person ... again, no shame if you do. But if you’re looking to date someone to develop a long-term relationship, you need to take things slowly and give the relationship time to develop. If it doesn’t develop, then you move on to someone else. But it’s a lot easier to move on when you haven’t built up your dream future with someone after just a few dates. It's also easier for you to spot red flags and make good choices about dating this person when you can see him clearly (which you can't do if you're in your excitement and fantasy). Take things slowly and cautiously, and evaluate whether this is someone you want to know better.
3. Use the first date to gather initial data. The first date is your first in-person opportunity to scope this person out. Do they show up on time? Do they spend the night talking about their ex? Do they get so drunk they can’t walk by the end of the date? Do they start asking you about sex right away? All of this is information about who this person is and what they’re about. Pay attention. People show you who they are pretty quick, and it’s important to believe them. If the person’s behavior doesn’t align with what you want in a partner, move on. Don’t assume you should have done anything differently. And don't make excuses for his behavior. The first date is when you put your best foot forward. If their best foot isn't great? Move on. There are endless fish in the sea. You’re not responsible for other people’s behavior. But you are responsible for eliminating people who don’t treat you the way you want to be treated, instead of hoping they change if you do something different.
There’s a lot to learn about building relationships. Learning how to start is incredibly impactful because you eliminate lots of future disappointments. When I learned how to take things slowly, I could eliminate men who weren’t a good fit for me fairly quickly. I didn’t over-invest myself in these men. So when it didn’t work out, it wasn’t that big of a deal. Before I learned how to go slowly, I rushed into things and I couldn’t see the other person clearly. That's when I ended up wanting to be with people I look back on now and thank God I didn’t end up with.
The sooner you end things with the wrong people, the sooner you open up to meeting the right people. Once I learned how to date, I felt empowered. I knew what I was doing. I could spot an emotionally unavailable man a mile away. And once I stopped wasting time on the wrong men, I pretty quickly met the man who is now my incredible husband.