I started dating while I was unemployed and felt insecure. I created a strategy to help myself feel more confident.

• I quit my job and then joined a dating app. 
• At first, being unemployed was exhilarating. But I started to dread it when dates asked about work.
• I had to find a way to deal with my anxiety and insecurity while dating.

On April 30, 2024, I quit my job. It was a job that barely required an ounce of creativity, a job that made me go, "Why do I need to crawl out of bed for this?" I craved change, passion, and a reason to wake up.

On May 2, 2024, I created a dating app profile that was equal parts funny, mysterious, and serious. I was ready to swipe and be swept off my feet. What I wasn't so ready for was the question, "So what do you do?"

Initially, the responses to my life choice were great. Dates would say things to me like, "Lucky you!" and "Congratulations! Having fun?"

But four weeks after I quit, I no longer felt like a free bird. I felt unemployed.

"I quit a month ago" didn't have the same impact as "I just quit my job!" The emphatic responses I'd once gotten turned into "Oh"s, followed by awkward silences.

But I kept swiping on and off, my insecurities constant, until I found someone I loved speaking to. He had more than a few green flags — and two dogs as a bonus.

And it wasn't just a stroke of luck. Before we matched, I put in the work to figure out how to date with the insecurities that cropped up along with my unemployment.

I strategized around my insecurities before dates

"What do you plan to do next?" a man asked me during our first conversation. It was a valid question. The real answer was that I wanted to chill and figure it out. But I hated how unambitious it might sound to another 27-year-old.

My insecurities snowballed and were reflected in my DMs, and I ghosted men who brought up the question.

I noticed that the complex was internal, triggered by "the question." So, before going on dates, I strategized. In person, I didn't have the option to 'leave the chat.' Plus, dates cost money, and my insecurities weren't going to be an added expense. I was going to deal with them.

First, I chose a venue that would be easy on my wallet — a local bar at happy hour. It took care of my anxiety about expenses and helped me feel a bit more in control. Then, I wondered what would make me feel more confident if a date asked me about my next steps.

I jotted down things I might want to do, like looking for freelance projects, part-time gigs, and enrolling in an online course. These things prepared me to answer the dreaded question and also prepared me more for my job search. I felt more ready to date, with my head high.

Something else hit me as I worried about being dateable without a job. The right person for me wouldn't put pressure on me to figure out my next job before I was ready. They would understand this phase.

While my next date did get it, we didn't hit it off on a romantic note. Still, I'd won against insecurities, at least in round one.

When I didn't feel interesting, I became interested

As the job market tested my patience, I had nothing significant to share with my matches except anxiety. But I realized I used to love talking about my work, and others would likely love talking about theirs, too. Since I didn't have anything new to report on the work front, I decided to start asking my dates about their professions.

For example, one of my matches ran a company that turned waste into accessories — something I knew nothing about. I asked him everything I could about his business, and he was engaged and inspired. The work discussion turned into conversations about life, and my joblessness didn't matter to either of us. Though the connection fizzled when he left for a business trip, I was back in the game, and I knew a lot about carbon footprints.

I learned that the right match will help me get over my insecurities

A few more weeks and job applications later, I started speaking to someone I really liked. He loved cooking, tennis, and sending gifs (ones that were actually funny).

Listening to him talk about his well-rounded, mindfully curated life, I realized that having a job isn't the only thing that could make me feel worthy. I could find a sidekick, a hobby, one that transforms me and becomes the source of endless conversations. After all, I didn't want our chats to end.

A week later, I enrolled in kickboxing lessons. Soon, I was starting each day by punching away my insecurities and anxiety. It was perfect.

My mental clarity was rising and so was my confidence. As I started feeling better, our conversations got better, too. One day at a time, I shared my worries about landing a good job, being unemployed forever, and running out of savings. He told me about his annoying manager. We'd brainstorm solutions for both our problems. Time flew, and I landed some interviews. He was taking revenge by beating his manager at tennis.

The swiping stopped, and we moved from messaging on the dating app to WhatsApp and FaceTime.

He's convinced a new job for me is right around the corner. In a way, his belief has diluted my insecurities. Some doubts still visit until I punch them down at kickboxing.

Two months later, my favorite thing is waking up to his "Good morning, ready to 'kick' start your day?" texts.

All the more reason to get out of bed.