I’m always analyzing dating because I hear so many people say how horrible it is. Deep down, I really want to be the person who helps it not feel so bad. To me, awareness is the key to a breakthrough. Once we understand the causes and effects of the struggles we’re facing, we can start figuring out how to fix them.
From my perspective, one of the biggest reasons dating feels so difficult is because so many people are dating with very low self-esteem.
What Is Self-Esteem?
Self-esteem is a person’s ability to achieve goals they view as important (competence), as well as the sense of being “good enough” or “worthy” (self-worth).
The piece that affects dating the most is self-worth. If you don’t believe you’re “good enough,” dating will feel like a constant battle. I know because I spent most of my life feeling inadequate. I often thought I wasn’t pretty enough, funny enough, or stylish enough. Instead of addressing those feelings, I learned to function in dysfunction. I masked it with false confidence, jokes, cute hairstyles, and nice makeup. But I couldn’t escape the effects of dating with low self-esteem. They showed up in every relationship.
These are the signs that you’re dating with low self-esteem.
You Try to Fit in a Box
When I was struggling with low self-worth, I obsessed over who my boyfriend’s exes were or which celebrities he liked. I thought if I could become like the girls he was drawn to, I’d have a better chance of being chosen. But pretending to be someone else isn’t sustainable. Eventually, you get tired of the act, or he realizes you’re not who you appeared to be. Either way, it never works.
You Only Attract What You Believe You Deserve
Life is all about perspective. For a long time, I believed I could only attract certain men because the ones I wanted wouldn’t want someone like me. My insecurities told me I needed to be slimmer, have longer hair, or lighter eyes. Because I believed that lie, I settled for men I didn’t actually want.
Later, I realized that the men I thought were “out of my league” had been attracted to me all along. But because I had convinced myself otherwise, I ignored their interest. That’s the power of belief. We’ll find ways to support whatever narrative we tell ourselves.
You Compromise Your Standards
When your worth is low, you start bending your values just to keep someone around. I once said I’d never live with a man before marriage and would only date Christians. But in my insecure seasons, I compromised those standards again and again.
Low self-esteem tricks you into thinking that compromising is worth it because this person might be your “only chance at love.” But every time you lower your standards, you chip away at your identity and happiness.
You Praise the Bare Minimum
Here’s a PSA: A man being faithful is NOT a luxury, it’s a requirement. A man taking you on a date is NOT a luxury, it’s a requirement. A man being a gentleman at all times, even when he is upset, is NOT a luxury, it’s a requirement. A man not pressuring you for sex is NOT a luxury, it’s a requirement. A man making time for you and being consistent with communication is NOT a luxury, it’s a requirement.
But when you’re dating with low self-esteem, you start treating the bare minimum as above and beyond. You say things like, “At least he calls me back,” as if that’s extraordinary. It isn’t. It’s the requirement.
You Settle for Comfort Over Happiness
There’s a big difference between being comfortable and being happy. Comfort is about familiarity; happiness is about true fulfillment. You can be comfortable and miserable at the same time.
Many people with low self-worth stay in unhappy relationships because they’re attached to the comfort of having someone, even though they know they’d be happier if they walked away. The fear of being alone keeps them in situations where they’re comfortable but not fulfilled.
You Blame Others Instead of Looking Inward
When dating keeps failing, it’s easy to start saying, “All men cheat” or “All men are dogs.” But often, low self-esteem keeps people from sitting still long enough to self-reflect. Instead of asking, What role am I playing in these patterns? They jump from person to person, seeking external validation.
Without that time alone to heal and reassess, the blame game becomes the norm, and the cycle continues.
You Begin to Feel Hopeless
Constant failed attempts can leave you feeling like love doesn’t exist, or that if it does, it’s just not for you. I’ve been there. Each failure chipped away at my confidence, until I felt hopeless and convinced that a good man simply didn’t exist. Or at least, not one who wanted me.
That hopelessness can be a result of dating with low self-worth.
Breaking the Cycle
So how do you rebuild self-worth? For years, I asked myself that question and got frustratingly vague advice like “love yourself” or “know your worth.” But no one ever explained how.
Eventually, I reached a breaking point. I couldn’t go through another relationship at that same level of insecurity. I needed to feel happy single, happy walking away from misery, and happy simply being myself.
It took time, but I rebuilt my worth. Now, I embrace who I am. I no longer entertain bare-minimum men, and I don’t idolize relationships. I just enjoy dating while being true to myself.
Conclusion
Dating with low self-esteem will always lead to cycles of compromise, frustration, and disappointment. But once you do the work of building self-worth, you free yourself to experience love in a healthy way.
If you’re struggling to break free from toxic patterns, my book How to X Your Ex is a great starting point. It digs deeper into how to let go of unhealthy relationships, heal, and rebuild your confidence so you never have to settle again.
