How to Date When Your Self-Esteem Isn’t So Great

This woman has low self-esteem but it ready to get back into the dating scene. What should she do?

Confidence is the key to attraction. Or so the saying goes. But in life and in dating, we’re not always feeling 100%. It could be that work is asking more of you than usual, you have family obligations that are worrying you, or you’re getting over a recent breakup. Maybe you’re just not in the right mindset about your body, your career, or yourself. But even though you’re not feeling amazing about yourself, that doesn’t mean you have to put meeting other people on hold.

It’s unrealistic to think you can only meet and get to know other people when you’re in the perfect mindset. But how do you make sure you’re seeking out healthy relationships and not engaging in unhealthy ones? Here are some tips on how to date when your self-esteem isn’t so great.

Tip #1: Be honest about where you are in your life.
Dating is all about putting yourself out there to connect with a new person. You’re not exactly spilling your deepest dreams (not at first anyway), but it’s about showing who you are to someone else. When you’re uncertain about who you are or what’s going on in your life, it may seem like you don’t want your uncertainty to show. But it’s normal to have doubts and fears, and it’s also normal to question yourself.

That doesn’t mean you should go into your first date spilling your guts about all your problems but don’t feel like you have to hide them away either. Part of building a relationship and intimacy with someone (or even just a friendship) is sharing the not-so-perfect sides of yourself. Chances are the person you’re with has their own doubts and fears. Or maybe they can give you insight from their own experiences to help you out.

Tip #2: Treat others the way you want to be treated.
You could be in the middle of dating someone when your confidence drops and you want to withdraw. But while taking the time to work on yourself, try not to leave people hanging. We’ve all had that experience where, after several dates that go well, the other person drops off the planet and doesn’t reply to your calls, messages, texts, emails, carrier pigeons, or whatever other forms of communication you dream up. It’s not a nice feeling, and despite how you’re feeling about yourself, you owe the other person the same respect you’d like them to show you. You deserve to find the right mindset to date and they deserve a simple message saying that you’re not in the right place to date.

Tip #3: Have your go-to date ideas and rituals.
When you get back into the game, there are a lot of things to think about—where to go, what to say, what to wear. To make it easier on yourself and ease the expectations and tensions, don’t feel like you have to stray from your go-to date spots, outfits, and rituals. Meeting at a bar or coffee shop is completely normal and might make you more comfortable than a date that’s a big production. On the same token, having an outfit that you know you feel good and confident can help too. If you have something picked out beforehand (and approved by a trusted friend), confidently prepping for a date just got that much easier.

Tip #4: Lean on your friends.
It’s hard to figure out when or where your self-esteem is going to take a hit and it’s even harder to dig yourself out. That said, it’s good to have people around for times like these. Your friends are the people who know you well and can tell you little things like what to wear on date, what to talk about, and when to get out there and start talking to people. More importantly, they’ll be there for you if a date goes south and you need someone to decompress with.

Tip #5: Don’t use other people to make yourself feel better.
There are parts about dating that are wonderful—feeling cared for, desired, and liked. Maybe even loved. Getting that kind of romantic attention from someone can make you feel a lot better about yourself. But when you know your self-esteem isn’t 100%, be careful that you aren’t counting on those feelings from someone else to make you feel good. Obviously, the person you’re with should make you feel happy but they shouldn’t be the only thing that makes you feel happy.

And remember, none of us are perfect and we don’t have to be perfect in order to meet someone who makes us happy. An important part of dating is getting to know other people. But an even bigger part is getting to know yourself in the process.

You’re a work in progress, and that’s a great thing to be.

Calvin Men

Freelance Writer

Calvin focuses on relationships and people when he writes. He’s given advice since high school when he told his friends what song they should send to people they like.

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