Advice and Insights for Modern Daters

Love Yourself

Gigi offers advice to a letter writer whose lack of dating experience negatively affects her self-esteem. 

Q. I am a special case. I say this because I am 31 years old and have never been sexually active or dated. I’ve never even tried a dating app, mainly because I’ve always felt ugly and like I don’t have anything to offer. I think my feelings are accurate because no guy has ever tried to approach me. What should I do? Where should I start?

Alice, 31, Washington DC

A. Hey there, boo — thanks for writing in. I know it must have been difficult to reach out and ask advice about something so personal. I appreciate you and your bravery. You’re taking a big step to finding solutions and I am so proud of you!

I want to start by assuring you that there is nothing wrong with being 31 and not sexually active or having a dating life.

What is a problem is the way you speak about yourself. To say you’re ugly and have nothing to offer is a really negative way to talk and feel about yourself.

What you are lacking is confidence. It isn’t a personality thing. I’m sure you are beautiful and amazing. The issue is that people can sense when you’re full of self-doubt and are directing harsh feelings inward. When you feel badly about yourself, you aren’t going to want to put yourself out on the dating scene, which means you don’t have dates, which means you feel badly about not having dates, which makes you feel even worse. It’s a vicious cycle.

Here is the thing: you cannot possibly expect to find love if you don’t love yourself. I know it sounds a bit trite to just say “love yourself,” but there are ways you can start to build self-esteem and grow internally.

You can’t find love if you feel like you have nothing to give. At least, not a love worth having. If you don’t love yourself and think you’re worthless, the only people you can possibly attract are those who also think you’re worthless. You deserve someone who thinks you are the best thing to ever happen to the world and nothing less.

I want to mention something that I think is important for you: we put far too much emphasis on physical looks. I am not saying you’re ugly or unattractive, not at all. What I am saying is that society thinks if you’re not “perfect” looking, you must be unlovable. We don’t give power and confidence to people of size, to people who don’t look like supermodels, and people who don’t fit into a typical standard of beauty.

Finding love is about so much more than that. Beauty fades, and what makes someone beautiful is subjective. It’s not what you look like that counts; it’s what you have in your heart that matters. Cheesy, I know, but I would choose someone’s personality over their looks any day.

Start by making a list of everything you like about yourself. I know you said that you think you have nothing to offer, but I promise that is not true. Is it your smile? Do you tell good jokes? Are you particularly good at one subject or sport?  Are you kind? Do you put others before yourself? Are you a good friend?

Think about it. I’m positive you will find several things that make you special and wonderful. Take a look at that list. Carry it with you. Remind yourself of all of those things that make you a good potential partner. Reread it whenever you’re feeling sad.

Finally, not to get super woo-woo, but have you considered seeing a therapist? Therapy is an excellent way to voice your internal concerns, and your therapist is there to help guide you through your struggles. What I love about therapy (yes, I go to therapy!) is knowing that this person is a professional who has been trained to deal with what you’re experiencing. I’m not saying you have to take medication or do anything you’re uncomfortable with, but having someone to talk to can make a huge difference.

I use TalkSpace, which is an app that connects you to a therapist, digitally. You don’t have to go into an office and can check in via text or voice message anytime you’re feeling down on yourself.

Ask yourself what you’re so afraid of when it comes to dating. Are you against putting yourself out there because you keep telling yourself you’re unlovable? It sounds to me like you’re using this excuse as a way to avoid dealing with the possibility of rejection. That’s just a part of life. We all get rejected sometimes.

Stop waiting for someone to approach you. You are the only person who can make things happen in your life. Get on dating apps. Get on Hinge! Talk to people, Make a move, even if you just say, “hi.”

At the very least, connecting with people on an app will give you a little ego boost. Sometimes we can all use that. Remember, you are amazing and there are people in your life who love and support you.

Don’t sell yourself short, babe.

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Gigi Engle, aka Ask Auntie Gigi, is a sex writer and educator living in NYC. Her work has appeared on Elle,  Teen Vogue, Bustle, Glamour, Allure, and Men’s Journal, Elite Daily and Thrillist. You can follow her on Twitter and Instagram @GigiEngle. Send questions to Gigi at


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