18 Things I've Learned After Going on Over 20 Dates

Updated 05/21/19
Natalie Off Duty

Dating is many things: fun, funny, exciting, enlightening, and sometimes awkward, repetitive, and laborious. One thing it isn't? Simple. It's the opposite of simple. But what else should we expect from what Merriam-Webster defines as "the series of social engagements shared by a couple looking to get married" and a single date as "a romantic appointment." Talk about pressure. Of course, we have a much more fluid understanding of the term today, which simultaneously makes it more fun and less consequential and rigid—but it also tends to complicate things further.

Personally, when I started counting how many first dates I'd been on in the past year and a half, I lost count at 20. And then I wondered why I was even counting them to begin with. I'm not one to measure and quantify my experiences, and I don't believe in relationship timelines. What matters to me is what I learn from each experience. Along the way, I met some not-so-great mates, I ditched many bad first dates, I had some fun flings, I experienced extreme disappointment, and I unexpectedly met my current partner.

When I began reflecting on these memories, I decided to write down the valuable ones that resulted in meaningful lessons. Eventually, it turned into a set of suggestions, reminders, and tips I wish I had while navigating the many phases of dating. So I broke down my 18 dating tips into three categories, including the first date, a few dates in, and a few months in. I promise it's not of the "rules for dating my daughter" variety. Hopefully, the dozen and a half dating tips below will help you come up with a dating rule book of your own.

Now let's begin with first-date advice.

For the First Few Dates

1. Boundaries are important.

It's okay if you're still figuring out what your boundaries are, just like it's okay to discover and enforce them mid-date. What I'm comfortable with and looking for fluctuates based on my lifestyle, my support system, my ambitions, and the chemistry between my date and I. While it's cool to be more flexible, I think it's important to make sure your date is being respectful of your boundaries, however you communicate them, every step of the way. If they aren't, consider walking away before you even place a drink order.

2. There will be many, many awkward moments, and that's fine.

Between taking an elbow to the trachea on a first hug, falling asleep at the dinner table, getting locked out of your apartment while being dropped off, forgetting their name, and literally lighting a table on fire, I have experienced every first-date nightmare you can imagine. When I first started dating, I was a ball of nerves because I was so afraid of feeling slightly uncomfortable or not having anything to say. But it's part of the deal, and once you accept that, you'll start to have so much more fun while also learning how to bounce back from slipups on your end or theirs.

3. If they're clearly looking for something different, call it off early.

Whether the other person was looking for something more casual or more serious than me, it's always felt better to call it off earlier rather than further down the dating line. I've even left a first date early, and while it was awkward, it saved both of us some trouble since we didn't have the same expectations or feelings.

4. Never tone it down; be as bold or as soft-spoken as you feel.

I can't tell you how many times I've been told to be myself, but not too much. First of all, what does that even mean? If we conceal our personalities or keep certain habits at bay to suit a situation, we aren't doing ourselves any favors since those things tend to reveal themselves sooner or later. So you may as well let them know who you are from the get-go.

5. Try to switch things up.

If you've been in the dating game for a while, try not to choose the same bar every time. I did this for a while out of sheer convenience. I'd just pick my favorite neighborhood dive bars since I knew they were good date spots and I could get home quickly if I wasn't feeling it. Not only did that lead to some awkward run-ins, but it also made me resent my beloved haunts. Once, two potential suitors turned out to be friends, and even worse than the same-bar issue, they found out that I saved their contact info as some interpretation of a literary classic, which I did with everyone I dated until this unfortunate turn of events.

A Light in August, Alexander Pushkin, Ichabod Crane, Dylan Thomas, and Benji (another Faulkner reference, of course) are just a few of my literary-inspired contacts.

6. Sometimes it isn't the right time, even if we think it is.

Whenever I've felt insecure (usually subconsciously) about any quirks, mannerisms, or tendencies, it was not the right time for me to be dating. I needed to get more comfortable with myself, my body, my intentions, and all that fun stuff, before I was ready to share those things with anyone else, especially where more emotions are at stake.

7. Whether or not they pay on the first date doesn't predict much.

In my experience, whether or not the other person pays has never been indicative of what kind of person they are. Some of the dates who paid were great first dates but never followed up again, while those who went Dutch ended up treating me on a later occasion, and one guy who forgot his wallet really did just forget his wallet. However, it is a nice gesture to at least pay for the first round if you planned the date.

A Few Weeks In

8. Make sure you're laughing.

You don't need to have an identical sense of humor, nor do you both need to be comedians. But if you aren't smiling and laughing together after a few weeks of dating and getting to know one another, I'd take note. This isn't important to everyone, but for me, we need to be making light of the weird things that happen to us and laughing at the silly moments and things we observe that may seem banal or commonplace to others. To me, that's just indicative of a special connection.

9. Don't over-invest.

I've never been a huge believer in dating a few people at once (remember when A Light in August and Alexander Pushkin became besties at my favorite dive bar?). Sometimes, you just happen to be seeing a couple people at once, and that's fine, too. But in my opinion, once you've been seeing someone consistently for a couple weeks, it's probably respectful to stop planning first dates. But it's a tricky balance. Here's an example: I started dating a great, perfect-on-paper person. They were super funny and accepting, they had a great job, and they were tall, dark, and incredibly handsome.

And they seemed to like me back. They suggested introducing each other to our friends after about a month of hanging out three times a week. Then, out of nowhere, they were gone.

And my friends are awesome, so I know that wasn't the issue. Even they were sad to see them go, which made it a lot harder on me. That's when I realized that I don't want to bring my friends, family, and other important relationships into the picture until there's a better sense of trust, even if things are going great. I need more time before I invest that much into the relationship. Just because it wasn't a big deal to them didn't mean I had to follow their pace.

10. Learn about their values early on.

If your values aren't in line, think about how that may play out later on. I've had some wonderful, meaningful experiences with people who were raised differently than I was and who felt differently about important issues, and that wasn't a problem. But if our core values weren't in line, things eventually fizzled. No matter how fun and sweet someone is, it's hard to care about or feel cared about by someone who doesn't value what you value.

11. Pay attention to your mood.

Do you feel lighter when you're with them? And even if things feel off or they do something that ticks you off, do you still feel good when you're with them? If yes, then that probably means you feel strongly enough that the little things don't throw you off track. It's a sign that you're building a genuine sense of trust and fondness for them.

12. Don't worry about labels, but don't intentionally avoid them either.

Like I mentioned earlier, it's fine to date other people if that feels right for you, but if you know that you don't want to see anyone else or you don't have the time to, that's okay too. Just remember the other person may not be on the same page as you, and that's okay. In these early stages, I think it's best to let the conversation come up naturally. This is because it can come off as combative or invasive, especially if you've never had any tricky conversations and don't know how the other person navigates and manages conflict or discomfort.

13. Try not to harp on the "rules" so much.

I can't even tell you how freeing it is to approach dating with a more laid-back mindset. Sometimes it's hard to control, especially if you catch feelings easily or early on. That being said, it's helpful to remind yourself that there's not a normal number of times to see each other in the first week, there's no set number of minutes to wait before sending them a text, and there's no telltale sign that this person is "the one" or that there's even such thing as "the one."

14. Take everything at face value.

Similarly, there's no secret language or hidden code to figure out. That's the thing with this stage in dating. There's a lot up in the air, and the only way to gauge how much or how little they like you, or what their intentions are, is to take it at face value until they give you a reason not to. If they abruptly seem uninterested, they probably are just abruptly uninterested. If they seem crazy about you, they probably are crazy about you. If they're somewhere in between, they're somewhere in between.

Instead of resenting or attempting to regulate the instability, just enjoy those butterflies, and let things unfold. And as confusing as their behavior may seem to you, yours probably confuses them too, which is why it's important to mean what you say and be clear and fair with your words so that they can feel safe to take it all at face value too.

A Couple Months In

15. Learn how to communicate.

Since everyone communicates differently, it's like learning how to do it all over again with each new relationship. To one person, a conversation feels like a confrontation and the other way around. But opening up good lines of communication is key to a healthy partnership. It's okay to falter and have some blunders, but letting emotions or reactions fester and making no effort to express yourself will only lead to delayed conflict.

Personally, I've often convinced myself it was better not to bring something up, no matter how important it was to me, simply because I was afraid of how the other person would react and I didn't want to put our relationship on the line. Because I liked them so much, the payoff (peace of mind and integrity) didn't feel worth the risk (they would potentially walk away). In the end, I chose the former, and while it broke my heart, I eventually picked up the pieces and felt more whole in the end. It probably wasn't going to work out for other reasons, but maybe if we'd both been more patient and calm with one another and tried to accommodate each other's styles of expressing ourselves while listening to others, we wouldn't have had so many hurtful miscommunications.

16. Ask yourself who you become when you're with them.

The last person I fell for taught me so much, and I would never have been in a place to meet my current partner if I didn't sit down and think about why it didn't work. I made a laundry list of reasons. None of them were as introspective as they should've been, and it wasn't cathartic in the slightest, but over a year later, it's proven to be extremely eye-opening. When I looked over those weepy little bullet points, I could see that one of the main issues, whether they encouraged it or not, was that I tried to be someone else for them, and they let me.

I've never deliberately changed myself to better suit someone else's projection of who they want me to be for them until I was with them. And I interpreted this shift as a sign of my strong feelings for them, but the truth was that they weren't right for me and that was too hurtful for me to process, so I repackaged it as something that felt controllable. It didn't help that they welcomed these little adjustments, and somewhere along the line, our relationship developed into a top-down dynamic reminiscent of that between a teacher and student.

But the difference is that a good teacher helps you discover tools to expand instead of shrink and also treats you like a teacher of sorts.

It sounds cliché, but it's so important to check in with yourself and to make sure this person makes you honor yourself and amplifies your good qualities while also accepting and maybe even cherishing your flaws so that you don't begin to erode your sense of self.

17. Protect your heart by letting it learn the hard way.

So you've been dating for a few months and you aren't interested in seeing anyone else. This person makes you happy and you get that warm feeling when you're together. That's great, and because it's so great, it can hurt if things don't work out. Here's the hard part, and I promise I don't mean it pessimistically: Things usually do not work out. Think about all the things that make you tick. You contain multitudes; we all do. And if that's true, your partner is bringing just as much to the table.

I'm talking about past experiences, subliminal intentions, deep fears and desires, ever-changing emotions, and sets of priorities. So as wonderful as it seems, everything can change in an instant.

But remember, that doesn't mean the happiness you once felt wasn't worth it, or that those moments didn't count, and that that person is horrible or tricked you. Sometimes things just don't work, but they are nice while they last. It takes courage to be vulnerable, so challenge yourself not to walk away out of fear that this won't last forever. If you do end up getting hurt, accept the pain instead of compartmentalizing it (without obsessing over it). Pain always has something to teach us, but we can't always access the lesson.

And pushing it away prevents us from learning and growing into better friends, partners, colleagues, and community members.

18. Forget timelines and all the dating advice you've ever gotten (including this).

It may seem sort of oxymoronic to advise you to forget about this, but the most valuable piece of advice for me has been to listen to myself. And more specifically, to listen to myself only once I've been in a place in my life where I trusted that inner voice to guide me and have my best interest in mind. I try to remind myself that even though my friends and family love me, only I can know what is best for me, and sometimes even I can't know that.

As someone who spends all her time with language and gets paid to put experiences into words, I have to admit that they aren't sufficient when it comes to capturing the resulting emotions, lessons, impressions, and ideas that come with relationships. All I can say with certainty is that we should listen to our own moral compasses, consciousnesses, and desires before we take note from a random drugstore magazine that tells us a quiz will reveal the guidelines and solutions to our love life woes.

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