"There's no way she'd go out with someone like me" - A long, long monologue on the eve of a confession

Introduction: A miracle happened on a matching app, but

The first date was a success. The second date was also enjoyable. With each passing date—the third, the fourth—the distance between us was definitely closing.

Our LINE exchanges continued every day, and the nights we spent talking on the phone increased. Spending weekends together was becoming the norm. Objectively speaking, this was clearly a "good vibe" relationship.

But inside my heart, a massive lump of anxiety was growing larger by the day.

"What if we just end up as friends?"
"What does she really think of me?"
"If I confess my feelings, won't I just destroy the relationship we have now?"

And above all, there was a voice whispering deep in my heart:

"There's no way she'd go out with someone like me."

Even though I changed my appearance, learned how to hold a conversation, and went on many dates, this deep-seated lack of confidence wouldn't easily disappear.

Today, I want to talk honestly about those days filled with anguish before I confessed to her. How much I worried, how lost I felt, and how I finally took that first step. All of it.

The fourth date: The peak of happiness and the beginning of anxiety

The fourth date was on a refreshing early summer Sunday. At her request, we took a trip to a seaside town. The two hours on the train, sitting side-by-side and chatting about trivial things, felt like a dream to me.

We had lunch at a seaside cafe, walked along the beach, and shared ice cream. In the evening, we climbed an observation deck and watched the sea turn orange together.

"It's beautiful, isn't it?"

When she whispered that, I was staring at her profile. Her face, illuminated by the setting sun, looked more beautiful than anything else in this world.

"It really is beautiful."

When I replied, she turned toward me and smiled, looking a little shy. She must have realized that I was looking at her, not the sea.

In that moment, my heart pounded as if it were going to explode. This is it. It has to be now. If I'm going to confess, this is the only moment.

But the words that came out of my mouth were,

"Shall we head back? Before the train gets crowded."

A truly pathetic suggestion.

She looked a little disappointed, but she nodded and said, "I guess so."

On the train ride home, I was consumed by self-loathing. Why couldn't I have confessed at that perfect moment? Why did I run away again?

Beside me, she was sleeping with her head resting on my shoulder, perhaps from exhaustion. Feeling her weight and warmth, I blamed myself over and over again in my heart.

The root of my lack of confidence: The 7 anxieties I was harboring

Why was I so unable to have confidence? Looking back now, the anxieties that dominated my mind can be broadly classified into seven categories.

1. Deep-seated complex about my appearance

Admittedly, I improved my grooming. I learned to be clean and presentable. But every time I looked in the mirror, what I saw was just "an ordinary guy who isn't handsome."

There must be many more attractive men around her. At her workplace, among her friends, and among the people she's connected with on social media. With options like that, what reason would she have to choose me?

2. Overwhelming lack of romantic experience

At 29, my decent romantic experience is almost zero. A faint crush in my student days and a few failures since becoming a working adult. That was the entirety of my romantic history.

On the other hand, she is someone who has experienced romance normally. I could sense the existence of an ex-boyfriend in our casual conversations. To someone like her, a romantic novice like me would surely be unsatisfying.

3. Anxiety about financial power

As an engineer at an IT company, my income is average. But when I think about the future, do I really have the financial power to make her happy?

Honestly, there were times when date expenses were tough. But I didn't have the courage to suggest splitting the bill, so I kept paying, pushing myself. Can I really say I want to go out with someone in this state?

4. Anxiety about communication skills

Admittedly, I can talk better than before. But that's because she is kind and creates an easy atmosphere to talk in. If we started dating and were together daily, wouldn't my lack of conversational ability be exposed?

I'm afraid of silence. I can't tell interesting stories. I don't have the confidence to keep entertaining her.

5. The curse of being "unpopular with women"

I stopped using the term "unpopular," but that feeling remained deep in my heart. There's no way someone who hasn't been popular for 29 years would suddenly become popular. There must be some catch.

Because she's kind, she might just be sympathizing with me. She might be going out with me because she feels sorry for me. Such paranoid delusions wouldn't leave my head.

6. The anxiety of not being able to read her feelings

I hear that women's feelings are complex. Even if they seem happy on the surface, their true intentions might be different. Is she really having fun when she's with me?

After a date, she tells me she had a good time, but that might just be a social nicety. When her LINE replies are a bit slow, I get anxious, thinking, "Maybe she's already bored of me."

7. Fear of failure

And the biggest anxiety of all was the fear of confessing and being rejected. Our current relationship is certainly ambiguous. But at the very least, I am able to spend time with her.

If I confess and get rejected, I'll lose all of this happy time, too. Wouldn't it be better to just continue this ambiguous relationship as it is?

The night before the 5th date: A sleepless night's monologue

Friday night, the eve of our fifth date. I couldn't sleep at all.

Lying in bed, staring at the ceiling, I repeated the simulation over and over in my head.

"I'll confess tomorrow, for sure."
"No, it might still be too early."
"But if I stay like this, we'll just stay friends."
"What if I get rejected?"
"In the first place, do I even have the right to confess, someone like me?"

I picked up the smartphone I'd left by my pillow and read through our LINE exchanges from the beginning. The message from when we first matched. The awkward conversation. The promise of a date. The process of our distance closing little by little.

"Just making it this far is a miracle, isn't it?"

Muttering to myself, I remembered my past self. The me who cried in front of the mirror. The me who could only wear black clothes. The me who couldn't even say "thank you" at a convenience store.

Compared to those days, I have certainly grown. But have I really grown enough to become a "boyfriend"?

I checked the clock; it was 3:00 AM. I have a date to meet her in six hours.

I buried my face in my pillow and let out a small shout.

"What am I supposed to do..."

Consulting a friend: Words that pushed me forward

The next morning, feeling dizzy from lack of sleep, I called a friend from my university days for the first time in a while. He was one of my few friends, someone who was already married with children—what you'd call a "normie" living a full life.

"Oh, Kenta. This is rare, what's up?"

“Actually... I have something I need to talk to you about.”

I told him everything honestly: my relationship with her, my anxieties, and the pathetic feeling of not being able to confess my feelings. He listened to me in silence until the very end.

“I see. So, Kenta, what do you want to do?”

“That’s... obviously I want to go out with her. But...”

“But you don’t have the confidence, right?”

“Yeah...”

On the other end of the phone, I felt like he gave a small laugh.

“Kenta, you’re selling yourself way too short. From where I’m standing, you’ve changed a ton. You used to be gloomy and hard to talk to, but lately, you’ve become more cheerful and can hold a normal conversation.”

“But even so, someone like me...”

“There you go with ‘someone like me’ again. Listen, Kenta. If a woman goes on multiple dates with a man, it means she at least doesn’t dislike him. In fact, it’s highly likely she has feelings for him.”

“Really?”

“Of course. Time is limited, so no one is going to meet someone they aren’t interested in multiple times. Besides, women don’t choose men based solely on looks as much as you think. They look at the whole picture—kindness, sincerity, whether it’s fun to be around them, and things like that.”

His words slowly began to loosen the rigid knots in my thinking.

“But if I get rejected...”

“If you get rejected, then you get rejected, and there’s always a next time. But if you don’t confess, you’ll regret it for the rest of your life, thinking, ‘If only I had gathered the courage back then.’”

“...”

“Kenta, there’s no such thing as a perfect person. The ‘man worthy of being a boyfriend’ you’re imagining is just a fantasy. What’s important is whether you have the feelings to cherish the other person. You have that, don’t you?”

“I do... I really do.”

“Then just tell her that. It’s that simple.”

After hanging up the phone, I took a deep breath. He was right. I had been denying myself too much. The time she spends with me might be a reflection of her feelings in itself.

The day of the fifth date: Determination, and the anxiety that still won't fade

The meeting place for our date was the usual spot in front of the station. She appeared wearing a light pink dress. It suited the late spring weather perfectly.

“Good morning. Did you sleep well last night?”

I gave a wry smile at her question.

“Actually, not really...”

“Oh, what’s wrong?”

“No, I was just thinking about something.”

The truth was, I wanted to say, “I couldn't sleep a wink because I was thinking about confessing to you,” but I didn't have the courage.

That day, we had planned to go to an art museum. It was a special exhibition she had wanted to see for a while. We walked through the quiet gallery together, looking at the works. Occasionally, we would share our thoughts.

Normally, I would have been able to enjoy this quiet time. But today, I couldn't focus on the art at all. My head was filled with thoughts of “when should I confess” and “how should I bring it up.”

“Kenta, are you okay? You seem a bit distracted.”

I was brought back to reality by her concern.

“Oh, sorry. I was just zoning out a bit.”

“Are you tired? Should we sit somewhere?”

Her kindness, conversely, made me suffer. Is it really okay for someone like me to have someone as kind as her all to myself? Isn't there someone more suitable for her?

We left the museum and decided to take a break at a nearby cafe. We sat at a window seat and ordered iced coffees. She ordered her usual cafe latte.

“Today’s exhibition was nice, wasn't it?”

She said that with a smile. Honestly, I barely remembered any of it, but I replied, “Yeah, it was.”

A silence fell between us. Usually, this silence would have been comfortable, but today it felt heavy.

“Um...”

Finally, I opened my mouth. But the words that were supposed to follow wouldn't come out.

"Hmm? What's wrong?"

She tilted her head slightly and looked at me. Her eyes were so direct that I instinctively looked away.

"No... it's nothing."

I ran away again.

Sunset Park: The moment that finally arrived

After leaving the cafe, we decided to take a walk in a nearby park. The park in the evening was bustling with people spending their time in their own ways—people walking their dogs, joggers, and people reading books on benches.

"Oh, that bench over there is empty."

In the direction she pointed, there was a bench under a large tree. We sat down there side by side.

The western sky was beginning to dye itself in shades of orange. The breeze was pleasant, and the leaves of the trees were rustling.

"It feels nice, doesn't it?"

She said that and closed her eyes. Looking at her profile, I thought to myself.

If I miss this moment, I might never get another chance.

Mustering up all my courage, I opened my mouth.

"Um... there's something I've been meaning to tell you since earlier."

"Yeah?"

She opened her eyes and turned toward me.

"I... well..."

My words got stuck. My heart was beating so hard it felt like it might burst through my chest.

"I... I like you."

I finally said it. But then, my words stopped there. I had actually intended to say, “Please go out with me,” too.

She looked a little surprised, and then her cheeks turned red.

“...”

A silence hung in the air. One second felt like an hour.

It’s no good. As I thought, someone like me...

The moment I thought that, she opened her mouth.

“You finally said it.”

Huh?

“Actually, I... I like you too, Kenta-kun.”

Conversation after the confession: Confessing my insecurities and her true feelings”

I doubted my own ears. She said she liked me, too. But I couldn't believe it right away.

“Really? But, someone like me...”

The words “someone like me” slipped out again. She looked a little troubled, but gave me a gentle smile.

“Kenta-kun, you said ‘someone like me’ again. I told you before, didn't I? I wish you’d stop that habit.”

“I’m sorry... but are you really sure about me? There are guys who are cooler, funnier, or richer...”

She shook her head.

“The reason I fell for you isn't because of those conditions. It’s your kindness, your sincerity, and how I feel at ease when I’m with you...”

“But I have almost no experience with dating...”

“So what?”

Her words were firm and clear.

"I'm not that experienced either. Besides, having a lot of experience isn't everything, is it? What matters is how we spend our time together from now on, right?"

I felt my heart gradually softening at her words.

"Actually..."

She continued.

"I was really anxious, too. I had no idea what you thought of me, Kenta. You seemed to enjoy our dates, but I didn't know if you wanted to be more than that."

"Wait, really?"

"Yeah. After our third date, I even felt down, wondering if I was a boring woman."

I was surprised. I never imagined she was feeling anxious too.

"That's why I'm so happy you confessed your feelings today, Kenta. I feel like we finally understand each other."

Anxiety about dating: Sharing honest feelings

"But..."

I still couldn't shake off my anxiety.

"I don't know if I can be a proper boyfriend. Date plans, gifts, anniversaries... I don't know anything about that stuff."

She chuckled.

"We can just figure that out together. I'm not looking for a perfect boyfriend."

"But..."

"Kenta."

She looked at me with a serious expression.

"The person I like isn't someone perfect. I like you, Kenta, because you're earnest, kind, and even if you're clumsy, you try your best. So, please just stay the way you are."

Hearing those words, tears welled up in my eyes. It's okay to just be myself. There is someone who accepts the imperfect me.

“I really like you, too. I’m clumsy, but I’ll try my absolute best... so please go out with me.”

This time, I was able to say it all the way to the end.

She answered with a beaming smile.

“Yes. I look forward to being with you.”

Epilogue: Confidence comes later

Now that some time has passed since that confession, I have some thoughts as I look back.

I realize that I didn’t need to have confidence from the very beginning.

What’s important is the courage to take a step forward, even while carrying anxiety and fear. The courage to show your imperfect self to the other person. And the courage to believe in the other person’s feelings.

I am still not a perfect boyfriend even now. I sometimes fail at date planning, and sometimes I make her feel anxious. But every time that happens, we talk it out and find a solution together.

The phrase “someone like me” hasn’t completely disappeared. But when I’m with her, that voice gets quieter. That’s because the fact that she chose me is a stronger support than anything else.

It’s not that you can’t confess because you lack confidence; rather, you gain confidence little by little by confessing. I think now that it’s okay for it to be in that order.

If I could meet the version of myself who confessed in that park at dusk with a trembling voice, I would want to tell him this:

“It’s okay. You are worthy of being loved. You did so well to summon the courage.”

My imperfect confession, from an imperfect me. But that was the true beginning of our story.

#Confession #NoConfidence #RelationshipAnxiety #SomeoneLikeMe #BeforeDating #GraduatingFromBeingUnpopular #RelationshipTurnaroundStory #Courage