Dating is Hard. Here’s What I’ve Learned So Far.

At 27, I am by no means an authority on relationships, having never been in a long-term, committed, healthy one. But I have traversed the dating landscape far and near, and as hellish as the scene may be, I have not yet relinquished hope that good men exist, and healthy, loving relationships are possible. In the meantime, I seek to shape myself into the best version of me for my partner. The version that is openly communicative, knows how to set and respect boundaries, is not afraid to have assertive conversations, knows how to give and receive love, and is extremely emotionally regulated. The road to love is not without challenges, but at the end of the day, we all deserve that special someone.

I have learned many lessons throughout my six-year dating career. My goal is to learn from each failed partnership, which are not truly failures, but learnings. Again, I am not an expert in healthy relationships, but here are some tokens of wisdom I have gleaned along the messy path of dating. Take what you will from it.

1. Communicate your needs, wants, and feelings. As a young girl in competitive gymnastics, I was taught that my needs, wants, and feelings were irrelevant. We were athletic machines, trained to perform and compete on the biggest stages and win medals. Talk of mental health and emotions was seen as “snowflakey” and “weak”, a luxury not afforded to us aspiring Olympians. So we were actively silenced, forbidden from talking during training, and kicked out of the gym for crying. The message imprinted in my 10 year-old mind: I don’t have a voice. It took me 10 years of therapy to unlearn this toxic script, and I still find myself falling into this trap in work and adult relationships. Well, for a healthy relationship to exist, you have to realize that your needs, wants, and feelings matter just as much as the other person’s. And ideally, you’d find a partner who makes you feel safe enough to express your desires and emotions– someone who genuinely cares.
2. Know how to manage your feelings. Dating and romance is an emotional rollercoaster for everyone, and especially for someone like me, who has a mood disorder. But it’s because of this very mood disorder that I’ve been forced to learn behavioral tools for emotional regulation, and I lean heavily on these tools whenever I feel frustrated, upset, hurt, or perturbed while navigating a new relationship. Things like steam rooms and hot tubs, journaling, therapy, meditation, focus on work, and communication. I truly believe that love and pain coexist, they are two sides of the same coin. If someone can’t hurt you, it probably means they don’t mean that much to you. That being said, it’s okay to experience ennui in relationships; for the ups to exist, there are necessarily gonna be downs as well. Don’t be afraid of the hard feelings. Instead of keeping it bottled up inside, just talk about it with your partner, and if you can’t resolve the conflict right away, don’t fret. You’re strong, you can handle difficult feelings, and you can sit with discomfort for a bit of time.
3. Set and respect boundaries. Boundary-setting has become a buzzword in mainstream American culture, and it is a very important concept to understand. Maintaining boundaries– things you can and can’t tolerate, your priorities, your sense of independence– is integral to healthy relationships. First step is to communicate them: “My work is my priority right now. I don’t have time to stay out late, I need to get adequate sleep. I hope you can understand that.” And then, work your way to a compromise. “But know that I care about you, and I make time for the people I care about. I’ll carve out time in my schedule to hang out with you on this day and time.” Hopefully your partner will be able to hear you out and respect your boundaries. And, of course, know how to respect their boundaries, as well. It goes both ways!
4. Temper expectations. It’s easy to get swept away by the fantasy of a great love when you first meet someone you really like. Are they the One? What will our kids look like? What kind of life will we build together? Been there, done that! And usually, you’re setting yourself up for disappointment when the reality falls flat, and none of your grandiose hopes and visions came true. It just wasn’t the right person. Well, you can spare yourself a lot of heartache by being realistic in the face of a new dating partner. Instead of thinking, “I hope he’s the One,” think, “Today’s date went well. I’m looking forward to the next one.”
5. Slow and steady wins the race. My dad gave me some sage advice when I was once again heartbroken after a failed romance, which also happened to be the most intense and passionate romance I had experienced, up until that point. He said, “Next time you date someone, leave a longer runway while getting to know them.” If an airplane doesn’t have sufficient runway to take off, it won’t be able to fly. If you fall too hard and too fast in a new relationship, it won’t work out. Chances are, you are possessed with lust rather than love, you have fallen in love with a fantasy or idea of that person, not who they actually are, because you haven’t taken enough time to truly get to know them before diving all in. So, take it slow. Let the relationship build organically, through conversations light and deep, shared experiences, texts and calls, all taken at a healthy pace. If you really want to build a future with someone, create a solid foundation. Not made of a pink cloud fantasy, but of bricks and mortal, iron and steel, respect and openness and honesty, communication and trust and balance.
6. Actions speak louder than words. I’ve had guys shower me with loving words and promises of a beautiful future, only to ghost me a week later, leaving me completely blindsighted. I’ve had guys promise me that I’d become their girlfriend one day, sometime in the near future, only to lead me on for months (and in one case, several years) without any intention of following through. It’s easy to say nice things, it’s harder to mean them. Examine their actions– what steps are they taking to stay true to their word? What kind of non-verbal efforts are they putting in to the relationship to make you feel safe and secure? And same goes for you, as well. What are you doing to show the other person that you care? Deliberate action speaks louder than empty, nice-sounding words.
7. Discern between what matters, and what doesn’t. Okay, so he stopped using heart emojis while texting you. Big whoop. That’s the kind of thing that used to bother me, and that alone was enough to send me into a spiral. Maybe it means something, maybe it doesn’t. Nowadays, I am much more discerning about what things matter in a relationship, and what things don’t. Is your partner being honest with you? Are they respecting your boundaries? Do they foster a space where open communication is possible, and you feel safe to express your mild irritation at the lack of heart emojis? LOL. In all seriousness, I had a guy once tell me that a relationship is much more than texting behavior and micro-mannerisms. In truth, all of it matters in a relationship, and you should communicate honestly when you experience a grievance, especially when dating someone new. Figure out where they are coming from, their love languages, their motives, their communication style. Once you have that data, you’ll have a better understanding of the things that matter in your relationship, and the things you’re willing to compromise and let go of.
8. Avoid passive-aggressive games. Ah, passive-aggressiveness. Something I think we all are guilty of. So they did something that was hurtful, whether intentional or not, and you feel butt-hurt and irritated and it’s affecting your emotional well-being. What you do next is very important. Do you stew silently inside and play passive-aggressive games? Send cold and dismissive texts, short and curt replies, or completely ghost altogether? Stay later at work and only come home to your partner when you know they’re asleep? Are you bad at conflict management and resort to petty games to communicate your discontent, instead of have an open and honest conversation with your partner? Are you working as a team player, or do you unilaterally call the shots on how to handle a fight? Bottom line: be an adult. Handle conflict maturely, and sometimes, you’ll realize that the “conflict” was all in your head, and they didn’t mean to hurt you– they honestly just had to put out a fire at work, or one of their family members was ill, or they were asleep all day, and that’s why they didn’t text you back in a timely manner, for example,
9. Never lose yourself in a relationship. I am a lover to the core. Behind the outward projection of confidence and strength and “Warrior Queen” energy, I am a sensitive soul with a marshmallow heart. I am, after all, an artist and a Pisces. If I love someone, I will give them the world. In the past, I would go overkill with this and completely lose sight of my passions, hobbies, and work-related goals, just so I could spend more time with my lover. When the relationship didn’t work out (perhaps in part because we were moving too fast and sacrificing too much early on), I looked at myself in the mirror with tear-stained cheeks and could not recognize myself. That is a mistake I will never repeat again. I will not compromise my value system to mold into another person’s “ideal woman”. You know you’ve found the right person when they allow you the freedom and space to be who you are. And, in turn, you give them freedom and space to be themselves.
10. Stay true to your values. What are your values, apart from your relationship? If I ask you what are 5 non-negotiable traits that matter to you, what will you say? For me, those things are: freedom, honesty, respect, ambition, and sobriety. If I ever find myself compromising on any one of these values to be with another person, it is a red flag.
11. Be a good listener. Hear what the person has to say with ears that reach to listen. Listen intentionally, actively, without jumping to a defensive reply. Listen to their words, which are a reflection of their soul. Especially when handling conflict. Our knee-jerk reaction when someone calls us out is to defend ourselves, and this comes off as dismissive and overly aggressive. They are not trying to insult you, they are just trying to talk it out. So hear them out, think for a moment, and then communicate your truth with kindness and respect for the other person.
12. Know when and how to apologize. A big part of open and honest communication is receiving feedback on when you’ve fucked up, and then humbling yourself and sincerely apologizing for hurting your partner. If you love a person, you wouldn’t want to hurt them, at least not deliberately. So here, self-reflection is important– give yourself a long, hard look in the mirror, and ask yourself how you can be better for your partner and what role you played in the conflict. It’s the most important thing, to take ownership of one’s faults and mistakes, asking for forgiveness, and promising to never make that same mistake again. And if that’s a promise that feels too big to keep, then brainstorm ways that you can work to a compromise. Or, maybe that’s a dealbreaker, and decide to walk away.
13. Yes. Know when to walk away. It’s always disappointing when things don’t work out with a person you thought you liked/loved. You have to grieve the loss of the fantasy. In some cases, that fantasy was close to manifesting into reality. In some cases, you lived the fantasy, and it was magical, you were in Camelot for a time, it was a great love. And then it fizzled out and ran its course. There comes a time at every relationship’s end where both partners must seriously ask the question, “Is the pain worth the love?” Or, “Do the good times outweigh the bad?” Or, “Should I settle for this, because starting over is just too painful?” Ultimately, it’s a decision you have to make for yourself, but only after you’ve given your best effort to make it work. Other times, walking away is easy. If they do something egregiously bad to hurt you, then of course respect yourself enough to walk away. But also, be kind to yourself when you feel compelled to stay. Relationships are nuanced, they are complex, otherwise, why do people stay in toxic relationships? They say, people are in your life for a reason, a season, or a lifetime. You can have a great love with someone who wasn’t The One. And that’s okay. The Universe paired you guys together because you had to learn something from one another. Just because it didn’t work out doesn’t mean it wasn’t a worthwhile ride, filled with the highest of highs and lowest of lows. Hopefully you learn from each heartbreak and emerge a better, stronger, wiser, more self-aware person.

Maybe you resonated with some of these tips, and maybe you didn’t. Again, I am no relationship expert—just a person with lived experience of love and heartbreak. I’m curious to hear your thoughts on how to foster emotional maturity in relationships. Leave a comment below and share your own tokens of wisdom from the messy path of dating.