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

Updated 08/16/19
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 the somewhat colloquial definition of dating that Merriam-Webster defines as "the series of social engagements shared by a couple looking to get married," which also defines 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.

When I started counting how many first dates I'd been on in one year alone, I lost count at 20. And reflecting on all of those initial encounters, what sticks out the most are the lessons learned from each experience. Along the way, I met some not-so-great mates, ditched many bad first dates, had some fun flings, experienced extreme disappointment, and unexpectedly met current partners.

With that said, I've collected all of these lessons and turned them into a set of suggestions, reminders, and tips worth sharing about navigating the many phases of dating. These 18 dating tips are divided into three categories, including the first date, a few dates in, and a few months in. Hopefully, they 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.

If you are too strict with your likes, dislikes, will/won't dos, you may be missing out on new experiences that could grow your personal edges or expand your worldview.

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 you're comfortable with and looking for in a partner will fluctuate based on your lifestyle, support system, ambitions, and the chemistry between the two of you. While it's cool to be more flexible, it's important to make sure your date is being respectful of your boundaries. How do you set healthy boundaries? According to the dating experts at Meet Mindful, speak up for what you need and what you're not comfortable with, but be careful of being too rigid. "If you are too strict with your likes, dislikes, will/won't dos, you may be missing out on new experiences that could grow your personal edges or expand your worldview," the website says. The site goes on to advise, "Stay curious and ask questions about things you don’t know about, even if you worry you may sound silly to your date. You never know where it may land you and sometimes it just may be exactly what you needed."

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 at the end of a date, forgetting your date's name, and literally lighting a table on fire, we've experienced every first-date nightmare you can imagine. Maybe you can relate: When you first start dating, you're a ball of nerves because you're 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. You'll also learn how to bounce back from slip-ups on your end, or theirs.

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

Whether your date is looking for something more casual or is ready to settle down, it's always better to call it off earlier rather than further down the dating line when it has become clear you two are looking for different things out of a partnership. I've even left a first date early because of it, and while it was awkward, since we didn't have the same expectations or feelings, it saved both of us some trouble.

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

Have you ever been told to be yourself, 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. Plus, wouldn't you rather be adored for who you are, rather than the person you're presenting? So, you may as well let them know who you are from the get-go.

5. Switch the location of your dates up.

If you've been in the dating game for a while, try not to choose the same bar every time. It's easy to do, yes. Out of sheer convenience, it's a no-brainer to just pick your favorite neighborhood dive bars to meet your dates at since they've been tried and true meeting spots (and you could probably get home quickly if you weren't feeling it.) Although, that might have lead to some awkward run-ins. Once for example, two potential suitors turned out to be friends, and even worse than the same-bar issue, they found out that this writer 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 literary-inspired contacts saved in my phone.

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

Whenever you feel insecure (even subconsciously) about any quirks, mannerisms, or tendencies, it may not be the right time to be dating. Maybe you need to get more comfortable with yourself; with your body, your intentions, whatever you're working through, before you are ready to share those things with anyone else, especially when more emotions are at stake.

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

Whether or not the other person pays on a first date has never been indicative of what kind of person they are. For example, some of the dates I've been on who paid were great first dates but never followed up again, while those whom we went Dutch with ended up treating us on a later occasion. There's also that one time a guy said he forgot his wallet really did just forget his wallet. However, a nice gesture would be to at least pay for the first round if you were the one who planned the date.

A Few Weeks In

8. Make sure you can laugh together.

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, take note. This isn't important to everyone, but finding the humor in the weird, bizarre, even upsetting things that happen to us, and the things we observe in daily life that may seem banal or commonplace to others, is what makes us human. And if you can do this together, that's indicative of a special connection.

9. Don't over-invest to soon.

Dating a few people at once isn't for everyone. Sometimes, you just happen to be seeing a couple of people at once, or are actively trying to put yourself out there and meet as many people as possible and that's fine, too. Take from the experts at eHarmony, "Look for someone you’re compatible with, someone who’ll be willing to put in the difficult effort of joining two adult lives in a meaningful way. And it takes time; you won’t find all that out on a first date, no matter how enchanting."

10. Learn about their values early on.

No matter how fun and sweet someone is, it's difficult to build a life with someone who doesn't value the same things you do.

If your values aren't in line, think about how that may play out later on. People have wonderful, meaningful experiences with people who were raised differently or felt differently about important issues. But if your core values aren't in line (for example, maybe you want to be a parent someday and your date is adamant of living life kid-free), eventually you'll have to reconcile these differences—if that's even possible. No matter how fun and sweet someone is, it's difficult to build a life with someone who doesn't value the same things you do.

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 most times? If the answer is 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 it was 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 (you are the Captain of your own love life, after all.) Just make sure to communicate what you want. And we get it, "The Talk," can be anxiety-inducing. "People worry that having these serious conversations may lead to conflict, which can prematurely end the relationship,” psychologist Marisa T. Cohen, PhD, an associate professor of psychology at St. Francis College tells Well and Good. Dr. Cohen goes on to tell Well and Good, "Be open to creating a shared understanding, and avoid ultimatums and timetables,” she says. “Just because your partner doesn’t see eye-to-eye with you at the time of the initial discussion, [it] doesn’t mean that they won’t eventually. Rather, this may be the first in a series of discussions.”

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

Here's a dating hack: Approach dating with a more laid-back mindset. It's absolutely freeing. Sometimes maintaining chill vibes is hard to control, especially if you are the type of person who catches feelings easily or early on. That being said, it's helpful to remind yourself that there's not a definitive number of dates you need to see each other in the beginning, or there's no set number of hours or days after a date you need to wait before sending them a text. Go with how you feel.

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 everything 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 what you can't control (namely, your date's feelings and communication style), just enjoy those butterflies, and let things unfold. And as confusing as their behavior may seem to you at first, 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 things at face value too.

A Couple Months In

15. Learn how to communicate.

Since everyone communicates differently, each new relationship requires learning how it works best with each new person you meet. Opening up clear, honest lines of communication is key to a healthy partnership. You may falter and even mess up in the process, but letting emotions or reactions fester and making no effort to express yourself will only lead to delayed conflict.

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

After you've been on a handful of dates with your prospective love interest, ask yourself, am I free and comfortable being myself around them?

For example, a cautionary tale. 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 even then, 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 helps you honor yourself and amplifies your good qualities, accepts and maybe even cherishes your flaws rather than erodes your sense of self.

17. Consider the end of a relationship a lesson, no matter how brief.

If things don't work out, consider it all for the best. 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. We're talking about past experiences, subliminal intentions, deep fears and desires, ever-changing emotions, and sets of priorities. People and circumstances change, and for those looking for a long-term commitment, for example, you'll want to find that person who is willing to grow and change with you.

But remember, if things don't work out, that doesn't mean the happiness you once felt wasn't worth it, or that those moments didn't count, and that the 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 don't always realize it right away when we're in the throes of heartbreak. And pushing the pain away prevents us from learning and growing into better friends, partners, colleagues, and community members. It's part of the process.

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

It may seem like an oxymoron, but perhaps the most valuable piece of dating advice is to tune in to yourself. Trust that inner voice to guide you and lead with your best interest in mind. Remind yourself that even though your friends and family love you (and will offer their opinions on your love life whether you want them to or not), only you can know what is best for yourself.

Although, if you're still in the market for some dating food for thought, consider these additional insights outlined in a 2018 Well and Good article. In it, Julie Spira, online dating expert and digital matchmaker, and offline dating coach Camille Virginia of Master Offline Dating had these words of advice. "I’ve encouraged dating coaching clients of mine to date outside of their comfort zone, initially with resistance,” Spira tells Well and Good. And, in today's digital age, be open to meeting people offline too. "Literally, I have been asked out on an airplane, at a coffee shop, at the bus stop. There is no magical place with other single people. The beauty is that they’re doing the same things you are,” says Virginia, who adds, "We’re meant to be around each other, get energy from each other, interact, have eye contact, and have in-person conversations. That’s how we functioned for hundreds and thousands of years.”

Leblon Leather Mules
Mari Giudicelli Leblon Leather Mules $605
Shop
Mini Acrylic Ark Bag
Cult Gaia Mini Acrylic Ark Bag $280
Shop
Women's 1996 Eau De Parfum 50ml
Byredo 1996 Inez & Vinoodh $175
Shop
Jotter
Postalco Jotter $12
Shop
Fine & Candy Charcoal Embossed Faux Leather Notebook $38
Shop
Notebook in Blossom Pink
Appointed Notebook in Blossom Pink $24
Shop
Pursama Vegan Hot Tub Bath Treatment $38
Shop
Valerie Confections Nature Is Slow Dark Chocolate Bar $10
Shop
Jeni's Splendid Ice Creams Salted Peanut Butter With Chocolate Flecks $7
Shop

Related Stories