Millennials Share How to Maintain Your Self-Esteem While Dating or In a Relationship

Who else has been taking a dip in a dating pool that’s contaminated with pee? With the City Boys movement, COVID-19, and the general ebbs and flows of finding yourself as a millennial, it’s been rough getting through the past few cuffing seasons. Navigating different factors of dating like getting out of your comfort zone, establishing boundaries, learning communication styles, and being assertive versus letting someone take the lead can all become super draining, especially when you feel like you’re not making any progress. 

I like to journal after going on dates to reflect and keep things in perspective. In a moment of feeling hopeless, I returned to my journal to find any patterns, or at least to see if I was learning anything new. After a bit of skimming, a specific passage gave me some pause. On another day I might’ve skipped over it because I’ve definitely recited similar soliloquies to my friends. But it felt different to read this time. Something about it didn’t feel right:

Shit. Is it me? It has to be me or something I’m doing, because ain’t no way I keep running into the same kind of guy. I should’ve BEEN made an appointment with a therapist. Maybe they can tell me why I keep doing this nonsense.

The voice of somebody’s auntie expeditiously popped in my head with a quick “Aht- aht. Cut that out.” It wasn’t the progress I was initially looking for, but more of the progress that I needed. 

I think any interaction in which you put yourself out there continually, invest time and energy, and expect mutual effort can cause you to question yourself. When you’re dating, you may ask yourself questions like: If I’m putting in the effort, why isn’t this person reciprocating? Is my best not enough? What do I need to change in order to get the response I’m looking for?

The same kind of uncertainty can be present when you’re in a relationship. Even if the relationship is stable, you can constantly wonder if your partner is satisfied. It’s easy to have tunnel vision focused on consistently contributing to the relationship to strengthen the connection and make it last forever. Am I doing enough to make my partner happy? Do I deserve to be in this relationship? Does my partner actually like me as a person?

And it’s so characteristic of self-doubt to show up loud and wrong. Investing energy into dating and relationships to ensure that they’re successful isn’t an unnatural thing. But it can leave us uncertain and negligent of ourselves. How can you pour from an empty cup? How can you show up for your partner and your relationship if you don’t show up for yourself?

It’s not over, but this year’s cuffing season has already taught me a lot. One thing in particular is that you can’t attach your self esteem to another person’s actions. I’m getting better at grounding myself in the fact that when dating, I’ll always show up honest, and I’ll always put my best foot forward.

I don’t typically hang on to the motivational Instagram speeches, but my explore page seemed to be tapping into my thoughts (as usual) and sent a message my way as I was reflecting on how we should maintain our self-esteem when dating or in a relationship. 

“Here’s how you can have crazy confidence with ANY kind of relationship. Be an asset. Add so much value to the lives of those who’re around you that you can see the tangible difference your presence makes. You see that enough times… if somebody doesn’t want to connect with you, you know, it’s okay. It’s their loss.” – @amandapittman 

To be clear, she’s not an advocate of burning ourselves out to prove our worth to someone. If you truly understand the value you can add to any relationship, you won’t keep questioning yourself if another person cannot see it. 

I wanted to gain some more perspective on the topic, so I continued the conversation with a few other women. Here’s what they had to say:

Gina – In a relationship for 6 months 

“To maintain self love I prioritize practices that make me feel good, like buying myself flowers, taking myself on solo out dates, and indulging in my passion projects that prompt me to exercise my creative talents. When I’m feeling particularly down, I allow myself to just feel the feels and let my partner know I’m feeling down. I found sharing this weight to be a relief because my partner offered a positive and different perspective that ultimately empowered us both to be more vulnerable with our feelings in our relationship as we love on ourselves and each other.”

Queenie – In a relationship for 4 years, newly engaged

“Find someone who actively encourages you to pursue your own interests, see friends, invest in your career, and take solo trips or trips with loved ones outside of your relationship. These things only get harder as we get deeper into our careers and pick up more caretaking responsibilities for kids and aging parents. A relationship that is practiced in mutually encouraging self-love is more likely to sustain that value throughout the relationship.”

Kendra – In a relationship for 2 years

“Communication and grace goes a long way in your relationship with your partner, but also in your relationship with yourself. We can easily lose sight of our needs when catering to others, especially romantic partners and a great way for me to maintain a healthy relationship with myself is to listen to myself and advocate for myself when I have certain wants and needs. Being with a person who also holds you accountable to do so is someone you should keep around. If they’re not advocating for you and your relationship with yourself, cut them off bestie!”


Featured photo: @theestallion/@meandsomebodyson_

Kymberly Deane is a writer, content creator, and storyteller based in Brooklyn, New York. Her passion for continual self-improvement and exploring new things has led her to become a health and wellness zealot, with a particular love for sexual health and wellness. She uses her writing to share the gems she discovers throughout her journey. 

Popular in Feel Inspired- Sisterhood