5 Dating Tricks for When You’re in a Slump to Boost Self-Esteem


Lately, I’ve been struggling with my self-esteem.

I’ve been hyper critical of my appearance, not feeling like I’m successful enough, and just all around wondering why someone would want to date me.

On top of doing therapy, and spending more time with myself, I’ve also gone on a few dates recently (which I wrote about here). We met through a friend and I wasn’t really expecting it to turn into anything, but now we’ve seen each other a few times, and I’m still struggling with feeling good enough.

The other night, we had drinks planned, and I just couldn’t get the right outfit, my skin was breaking out, I was feeling bloated — not in top shape for a date.

The idea of bailing and getting into PJ’s and crawling into bed seemed much more appealing.

But I’d committed. I knew I had to hype myself up and get out of my own head. It also ended up being a really fun evening, so I’m glad that I did.

Here are a few things I do to spin my slump around:

  1. I put on a go-to outfit that was comfortable and sexy. When I’m feeling bloated or insecure about my body, I always wear my black skirt and a black body suit with tall boots. It’s such a comfortable outfit and it still looks dressy. I recommend having one or two classic outfits that you know you will always feel good in.
  2. I put on a dating reality show and have a glass of wine. There are so many fun dating shows— “Celebs Go Dating,” “First Dates,” “Dinner Date” — and they always make dating feel lighter and exciting. They remind me that dating is just about getting to know another human being. A glass of wine helps ease some of my nerves. (Though, if you struggle using alcohol as a crutch, a shot of espresso also works nicely.)
  3. I listen to tunes on my way to the date. I have a “pump up” playlist that always makes me feel good and gets me out of my own head.
  4. On the date, I focus on the other person. People like someone who is genuinely curious about them. Also, if you’re not feeling great about yourself, like you can’t toot your own horn right then, it takes some of the heat off you.
  5. I pep talk in the toilets. When I go to the bathroom, I take those five minutes alone to re-ground. I do deep breathing exercises. I tell myself that nobody is as critical about me as I am about myself. It helps to have a mantra to repeat to bring you into the present moment.

In general, I try to remember that positivity is contagious. If you’re laughing, you’re curious about the other person, asking questions, keeping things light, it makes you more attractive.

Wearing something you’re comfortable in, and having a little prep time before the date to get yourself in the mood, always helps too.

What are your dating tips for when you’re not feeling so great? Send them my way in the comments!

If you liked this story, consider joining and becoming a Medium Member for $5/month, here. You might also like:

Previously Published on medium

Join The Good Men Project as a Premium Member today.

All Premium Members get to view The Good Men Project with NO ADS.

A $50 annual membership gives you an all access pass. You can be a part of every call, group, class and community.
A $25 annual membership gives you access to one class, one Social Interest group and our online communities.
A $12 annual membership gives you access to our Friday calls with the publisher, our online community.

Register New Account

Log in if you wish to renew an existing subscription.

Choose your subscription level

By completing this registration form, you are also agreeing to our Terms of Service which can be found here.



Need more info? A complete list of benefits is here.

Photo credit: Shutterstock

The post 5 Dating Tricks for When You’re in a Slump to Boost Self-Esteem appeared first on The Good Men Project.

Older Post Newer Post