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Caitlin Kilgore

Updated: 02/01/2022

Dating has a way of pushing our vulnerability threshold to the edge — it's hard to put yourself out there and face rejection, let alone deal with the ups and downs once you actually connect with a new person.

Often we search outwardly for something to provide the confidence we need to enter into the uncertainty that is dating when really, the bravery lies within; per to the experts THE WELL spoke with, cultivating confidence begins with how you treat yourself.

So whether you’re new to dating, a seasoned dater or simply in need of some self-love reminders (Hint: you’re beautiful with or without a partner), read on for advice from three body-positivity thought-leaders.

By the way, you can join these three expert panelists (and more) at The BodCon, a virtual body-positivity conference taking place February 27, 2022 to hear them discuss the nuances of what it means to practice radical self-acceptance.

Meet the Experts

Alexandra Stewart:

Alexandra is a Chicago-based body-positivity influencer. She is the creator of the blog Sassy Confetti and host of the dating podcast Swipe Fat, where she and co-host Nicci Nunez discuss what it's really like to date while plus size.

Clara Dao:

The 23-year-old digital creator promotes body positivity for small-chested and "skinny" girls. Despite experiencing trolling for her lack of curves, Clara uploads body-positive videos to boost her confidence and encourage other women to celebrate themselves as they are.

Lisa Schoenberger:

Lisa has carved out a name for herself in the fashion industry as a voice for size inclusion, representation and body diversity. As someone living with a chronic illness, lipedema, as well as anxiety and depression, Lisa struggled to accept her body, but she now truly knows that she is beautiful, inside and out.

Confidence can feel like an elusive, abstract term — what does it mean to you, and how do you cultivate it?

ALEX: So often people equate confidence with feeling hot or sexy. Of course, it can be those things, but for me, confidence is how I feel as a whole. It's about acknowledging all the amazing qualities we bring to this world and showing that in the way we interact with others.

CLARA: To me, confidence is knowing myself, feeling secure in myself and accepting things about myself that I cannot change. It’s [knowing that] I'm beautiful and worthy in my own way and everyone else is also beautiful and worthy in their own way. We are all equal. 

I cultivate confidence by reminding myself every day how beautiful I am (both inside and outside), what makes me special and all the amazing things that I'm capable of doing and achieving. I find that the more I focus on myself and my own journey (not comparing myself to others, not spending too much time on social media), the more secure and confident I feel.

LISA: Confidence is a journey that you’re going to take every day for the rest of your life. Some days will be good and some will be bad, but learning to be confident is about how you handle the bad days — focusing on the good things, reframing the way you think about yourself and not letting what others think limit your perspective. You have to put in the work because [when we] spend a good portion of our lives hating our bodies… so much needs to be unlearned.

Alexandra Stewart, Photo Credit: Sassy Confetti

How do you bring your most confident self forward when dating?

ALEX: Before I go on a date, I like to think about the thing that makes me the most passionate because that's usually the thing that I feel most confident talking about — it's what lights me up. I try to channel that energy on a date. When you're passionate about something, it is palpable and attractive to others.

CLARA: I always remind myself that I am capable of giving myself all the love and validation that I need and crave from a partner. This single affirmation alone has helped me feel so confident and at ease when I get to know someone new, and not let the infatuation and excitement of new love take over me. The relationship you have with yourself determines the quality of all other relationships you have in your life.

LISA: You need to block out the noise and the nerves that come with dating. This person has likely seen you, read your profile, talked to you… they are clearly interested for a reason and they likely see something in you that you may not see in yourself. Don’t be afraid to hype yourself up. If things don’t work out, that’s ok too. It’s not a reflection of you — some things are just not meant to be.

“I always remind myself that I am capable of giving myself all the love and validation that I need and crave from a partner.”

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When insecurities pop up — whether on the first date, second date or a couple months into a relationship — how do you deal with them?

ALEX: First and foremost, I try to find the root of the issue. Why am I trying to find reasons they're not going to like me? What am I scared of ultimately? If the person I am with is making me feel that way, that is a red flag and should be dealt with quickly. Am I internalizing it or are they making me feel unworthy? [These are] two very different streams of thought!

CLARA: I remind myself that no one cares about my insecurities as much as I do. Maybe they don't even notice, so I shouldn't waste my time worrying and feeling bad about something that honestly doesn't matter. Usually, telling myself this [helps] me snap out of my insecurity and feel confident again.

LISA: Communication is always key, especially early on in a relationship. We aren’t mind readers, so if something makes you insecure, it’s best to be honest and talk about it. It’s easy to focus on our own insecurities while forgetting that the other person is going to have their own insecurities. By creating an environment where both of you feel safe and comfortable talking, it doesn’t become this big scary thing. Strong communication makes for a strong relationship.

Any tips for letting go of judgements, fears and insecurities when dating?

ALEX: In the beginning, I think it's a lot of inward thinking and building yourself up — not putting so much weight on any one relationship is very helpful as well. Once you're in a longer term relationship… lots and lots of communication. The only way we can let go of fear and insecurity when dating is talking about it with our partner and not letting it fester.

CLARA: Know that there is always somebody out there for you (actually, there are a lot of people) who would totally be into you and value you for who you are. Don't feel like you have to change to fit into some sort of ideal so that more people could find you attractive — you're more than enough already!

LISA: I like to think of the saying “you can’t judge a book by its cover.” We are inherently complicated, unique, wonderful beings that have so many layers that make us, us. So embrace who you are, know your worth and have fun.

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Clara Dao, Photo Credit: Clara Dao

With dating apps or online dating, there’s often this pressure to curate the perfect profile with super flattering pictures. What tips do you have for letting go of this pressure?

ALEX: Ultimately, building an online dating profile should not be anxiety inducing. It should be fun! So show the fun sides of you — your hobbies, you out with friends, etc. Just make sure you show your personality and all aspects of it!

[For] plus size women, we don't really have the luxury of wanting to look uber flattering. We almost have to do the opposite so we don't ‘fatfish’ people. On our podcast, Swipe Fat, [my co-host Nicci Nunez and I] recommend not using any filters (deceiving!), always showing a full body shot and showing you next to friends who are straight size so they can see a comparison. And don't forget: A close up photo of your face should be picture number one!

CLARA: That pressure is real and understandable, but we can let go of it by reminding ourselves that we're not in competition with anyone. As long as you put your authentic self out there and you have good intentions, you will always find someone who is meant for you.

LISA: For a long time, I felt that I had to have the best photos on my dating profile. But over the years, I’ve found that my partners actually prefer a natural photo of me — we’re talking no makeup, hair in a bun! My advice? Share all sides of you in your photos, there’s nothing more attractive than being genuine.

Attraction and beauty are completely subjective. What advice do you have for embracing what you’re attracted to and letting go of what we’re told to like or not like?

ALEX: I am one hundred percent guilty of trying to date people who I think will find me attractive and not the other way around. I did this for years! And you know where that got me? A lot of miserable dates. Swipe right on people you would want to kiss. Plain and simple. Trust me, it'll result in a lot better dates!

CLARA: Ask yourself: Why is it hard to let go of what people expect you to like? This is your life and what you find attractive is none of other people's business. If you find certain things about a person attractive, just go for it! But keep an open mind if you meet someone who's genuinely great but may not quite fit your "ideal type.” You never know what could potentially become a great relationship down the line.

LISA: As a fat woman, this is something that I have dealt with my entire life. We live in a society where people are told that it’s not okay to be attracted to a fat person. We live with the fear that we are being fetishized or sexualized because again, society has told us that is the only reason that someone can be attracted to us.

These antiquated standards of beauty and attraction create a host of insecurities in all of us that can limit us when we are looking for potential partners. My advice is to go after what you want. There is nothing wrong with who you are attracted to, who you find beautiful and ultimately, who you want to be with. That is your choice and you need to choose what makes you happy.

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Lisa Schoenberger, Photo Credit: Rebecca Northcott Photography

When things start to get intimate, and insecurities around your body arise, how do you quell the critical inner voice? How can you walk into these situations your most confident self?

ALEX: I try to remember that we are both just people — that person I’m with also has insecurities. When I look at it from that outsider perspective, it's easier to feel confident in my own body, or at least confident that we are both just two people with insecurities in front of one another.

CLARA: Remind yourself that most of it is just in your head. The person that is with you is attracted to you and they don't see you in the same critical way that you see yourself. Remind yourself that you are beautiful and sexy in your own way — speak to yourself like someone you love.

Another thing that really helps me feel a lot more comfortable in my skin is to look at my naked body when I'm by myself and say positive affirmations. The more I look at my body, the more I get used to it and eventually learn to embrace and accept the parts that I may not have liked at first.

I also dance to my favorite songs in the outfits that I love — ones that make me feel hella sexy — and just let loose and dance in front of the mirror! It’s not only super fun, but it’s also helped me feel so much more comfortable with my body. Everyone should try this at least once!

LISA: Do things for yourself prior to intimacy that make you feel confident and put you in a positive mindset. That could be getting your hair done or a mani/pedi, buying some new lingerie, creating a playlist and dancing or spending some time setting the mood. We all deserve intimacy and the joy that comes with it, so be present, confident and enjoy it.

"Speak to yourself like someone you love."

What is one piece of advice you want everyone to know when it comes to dating, relationships and intimacy?

ALEX: Dating should be fun. For years and years of my life I found it so miserable because I treated it like a job. My first dates were like bland interviews. I went out with people I wasn't even attracted to. Looking back on it, I think I thought that was all I deserved. Now [that I have] a much healthier mind frame about what I bring to the table, who I am actually attracted to and what I deserve, I can go on dates that are actually fun. So remember, dating should be fun! And if it's not, that usually means it's time for a break and a reset. Nothing wrong with taking breaks!

CLARA: Work on your relationship with yourself. By loving yourself first, you know how to value yourself and feel confident even when facing rejections and heartbreaks. You've got this! Keep being you!

LISA: You can’t be afraid to put yourself out there. It’s hard and it’s scary to be vulnerable but without risk, there is no reward. I spent a good portion of my life thinking that I needed to be thin before I was worthy of dating, a relationship and intimacy. Not only was I wrong, but I missed out on a lot and I can’t get those years back. I wish I had been kinder to myself.

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