#howimend: Ilyssa Bernstein of Lipstick Confessions On Dating In The Digital Age


Ilyssa Bernstein is the woman behind Lipstick Confessions, a crowd sourced Instagram project where she turns your hilarious and frustrating dating stories into poetry. She is based in New York City, but receives stories from women all over the world. 

If you think back to the first time you were heartbroken, what advice would you give to that younger version of yourself?

"My first and most significant heartbreak happened just before my 17th birthday. We had been together two years. After our first year together, he went off to college while I remained at home and in high school. The distance, like a disease, infected our relationship. Slowly at first, but after time, it was impossible to ignore. We were growing up and growing apart, and I wasn’t willing to accept it. He was.

The advice I would give myself: This is the end of “us”, but this is not the end of “me”. In fact, this is a new beginning for me. The love and friendship he and I shared was real and it was honest. I would make my younger self promise to always remember how he treated me, loved me, and spoke to me – and never to accept anything less. I would follow that by saying the best medicine for a broken heart is time. Mending a broken heart isn’t a process that can be rushed. New prospects too quickly are often just bandages, and bandages may mask your pain for a bit, but only time can truly heal you."

What has heartbreak taught you about yourself?

"Heartbreak, and really being single in general, has taught me independence. You can never rely on anyone or anything to bring you happiness but yourself. It has taught me how to not only be comfortable being alone, but how to enjoy spending time alone. Whether it’s going for a run, seeing a play, or visiting a museum, if it’s something I enjoy, I’ve learned I don’t need a partner to do it with me. It has also given me courage to put myself out there with my writing, something I’ve always wanted to do but was afraid of failure."

What are your rituals during a breakup? What things/practices/people helped you mend?

"I haven’t met anyone who has made me feel the way my first love made me feel all those years ago, but that hasn’t stopped me from trying to find that feeling again. Although it hasn't happened yet, I still believe that one day I will meet the right person, and I am not willing to settle. As part of the dating app generation living in New York City, you would think dates are plentiful. And, well, yes – they are – but finding a connection has proven much more difficult. I was tired of meeting men who broke their promises, communicated with women through a misogynistic lens, or men who more often than not just disappeared into oblivion – never to be heard from via text or phone call again. I thought I was the only one feeling so unsatisfied and disappointed by the dating scene. But I soon learned these same concerns were inhabiting the minds of many single women I knew. I was not alone, and neither were they. It was at this moment I realized that as long as I was being "me" on each date, I wasn’t doing anything wrong. I wasn't the problem, and there wasn't anything about me I needed to change. This epiphany helped me mend. I wanted to help other women mend as well.

I started turning both the comical and the frustrating dating anecdotes of myself and my friends into short poetry. I share each poem on an Instagram account I call Lipstick Confessions. Every time I turned one of my own stories into poetry, I felt lighter and happier. My hope was that other women facing similar struggles would find the same comic relief and freedom I did through my poetry. Soon, women from around the world began sharing their stories with me, trusting me to tell their tale in poetry form. Learning the stories of all these women has helped me feel less lonely, as I continue to navigate through today's complicated and often disappointing dating landscape."


What’s the biggest lesson you’ve learned about love so far in your life?

"The most important person in your life you should love is yourself. I know it sounds cliche, but I believe it's true."

Do you think exes can be friends? Do you stay friends with your exes on social media?

"I think this can only be answered on a case-by-case basis. I believe being friends with an ex is possible if one or both of you were in love with the other, if the break-up was respectful, and if neither party is still in love with the other. You may always love your ex, but being in love and loving someone are very different. From my experience, getting to a place where rekindling this kind of friendship is possible may take several years.  I have exes of both these circumstances that I am friends with on social media.  I believe being friends with an ex is less realistic if the break-up involved one partner disrespecting the other. I have exes of this circumstance as well, and I am not friends with them on social media."

What keeps your heart open, despite the heartbreaks you’ve had in your life?

"Sometimes it's really hard to keep my heart open. Sometimes I think maybe it's just not in the cards for me. But nothing good ever comes from breeding negativity. The more I focus on achieving self-happiness, the more I find myself believing that I will find that feeling again."