How Making the First Move in My Dating Life Increased My Confidence

By Stephanie Yeboah 

I’ve been passive throughout the majority of my dating experiences. As a very introverted person, it can take some time for me to show my true personality, and that includes mustering up the courage to speak first. When I signed up to dating sites or for apps, I waited for men to send me a message. Sometimes I’d send a vague meme in the hopes that a match would get the hint and begin a conversation. I was never the one who made the approach when it came to potential dating scenarios. 

Part of my reticence was because as a teenager and young adult, I lacked a huge amount of confidence due to being plus size. I never had any problems with my body, but others seemingly did. I had a match write social media commentary about our dates using fatphobic language to describe me. A number told me my weight was unattractive to them, leading me to develop a complex over time—and to believe that I was unworthy of love, desire, or affection. I grew up watching my friends and peers date, flirt, start relationships, and fall in love. I was happy for them, but I also felt a palpable sense of loss for myself. I wanted that, too. But instead, in my romantic relationships, I tended to settle for dating men who saw me as nothing but a way to explore and satisfy their fatphobic and fetishistic desires. 

Over time, it seemed like the type of man I was interested in— intelligent, open-minded, kind, and passionate—would never approach me first. I became even less confident and more apprehensive about dating. Putting myself out there was daunting, and because I always assumed that I knew how the interactions would turn out, I’d chicken out every time. This would manifest itself in other ways outside of dating, such as networking or speaking to others at events. I would become incredibly shy and uncomfortable knowing that I might have to start a conversation. 

Then, in 2018, I joined Bumble. I realised that the only way I would be able to form romantic connections and have fun dating was if I took the bull by the horns and did something about it. I had made a goal to take more risks and undertake things I’d never done before, and that included making the effort to approach men first, regardless of the consequences. As a woman on Bumble, only I can make the first move, so I decided to throw caution to the wind and go for it.

I scrolled through profiles, trying to find someone with a kind face who I thought might reply to me. Finally, I found a guy who didn’t live too far from me who looked and sounded decent from his profile. I swiped right, and anxiously waited to see if he would swipe back. Moments later, the match notification popped up on my phone! I was filled with dread once more as I opened up the app and pondered on how to start the conversation. Would a simple emoji do? What about a funny meme? Sending a mere ‘hi, how are you doing?’ seemed too basic—I had to think of something better. I went on to spend nearly an hour scouring his profile to find something to talk about. 

Eventually, I settled on asking him five facts about himself. It was simple and slightly cheesy, but I reckoned it would get the job done. I sent the message; a sense of finality yet exhilaration ran through me. I put my phone down and busied myself for the next few hours, thoroughly expecting to reopen the app to find that I’d been unmatched.

To my surprise, I received a response: a detailed paragraph complete with a few laughing emojis. I felt a massive sense of relief alongside a slight confidence boost. It was literally the least the guy could do, but getting a response as opposed to being automatically unmatched meant a lot to me. It was at that moment that I realised that putting myself out there and sending a message first wasn’t as intimidating as I first thought.

Although the conversation eventually fizzled out with that guy, I decided to try again and again, thinking of witty, random, funny, smart intros to send and taking note of the kinds of intros that were giving me the highest success rate. (Answer: the boys I matched with seem to love wit, direct questions, and funny memes.) I realised that I had been linking my dating life too closely with my self-confidence, and taking each unmatching or ghosting as a personal slight. I started to see that despite there still being matches out there that took issue with my looks, it had no bearing on my worth as a person, or the depth of conversation I was able to bring to the table.

Instead of being passive and only opting for men who I thought may accept how I looked, I would swipe on men that I assumed wouldn’t, just on the off chance that they may swipe for me. I saw myself as worthy of being liked, and started acting that way.

For the most part, the majority of my matches didn’t amount to much, but I realised that I was enjoying dating for the first time ever. Even as an introvert, I was having fun putting myself in the driver’s seat and actively taking part in conversations. After a few months of this, I decided to try out my newfound confidence and ability to put myself out there in other parts of my life. I work within the influencer and fashion community, so I started approaching peers by complimenting them on their outfits, makeup, or pieces of content. Being able to speak first and make someone feel good about themselves in turn made me feel really good about myself, and definitely added to the confidence I was slowly developing. 

These first moves allowed me to make even bigger moves, and I began hosting panel events and giving speeches. I realised that being the first to speak when it comes to dating—either via an app or on a night out with friends—is something I now like to do, especially if I prepare what I’m going to say beforehand. I’m no longer scared of being rejected or laughed at when dating, and even if I end up embarrassing myself with a goofy anecdote or comment, so what? I know that I’m worthy—of a date, and of love.