Chapter 1 · He Regretted After I Helped Him Win Her

Back when I was dead broke, I started moonlighting as a relationship coach on a secondhand marketplace app.

My childhood friend, Ethan Carter, ended up being my very first client.

He had no idea it was me behind the screen.

His first message after placing the order was:

[I've had a crush on this girl for five years. Lately, someone else has been chasing after her, and I'm scared someone else might win her over. I want to confess, but I'm worried that if I fail, we won't even be friends anymore. I'm so torn.]

My heart started pounding as I read his message.

I was the girl he'd known the longest.

And yeah, there really was someone chasing after me lately.

So, was he talking about me?

With a bit of selfish hope mixed in, I encouraged him to take the leap and tell the girl how he felt.

He agreed to follow my advice.

He even mentioned that her birthday was in two days, which sounded like the perfect opportunity.

My fingers froze over the keyboard.

Wait, two days from now?

Hold on, wasn't that my bestie's birthday?

*****

I spaced out for a second.

My phone kept buzzing.

He messaged again: [There's a rooftop restaurant downtown with a killer view of the city lights. I'm planning to take her there for dinner and confess my feelings.]

The restaurant he mentioned was called Cloud Nine.

I was the one who recommended it to him.

I told him the night view was gorgeous, and that I'd definitely go there someday when I could afford it.

Back then, he scoffed and said, "A meal there costs over 300 dollars? Only suckers would go there."

Who would've thought he'd end up being the sucker himself so quickly?

I gave a wry smile and typed: [Congrats. Isn't that place super expensive?]

His reply came quick and cheerful. [Confession's gotta be formal, you know.]

We were still chatting when my phone buzzed with a new WhatsApp message.

It was a message from Ethan.

Ethan: [Can you lend me 300 dollars? I'll pay you back next month.]

I stared at the message.

I couldn't help but laugh in exasperation.

I couldn't help but think: wait, so he was confessing to someone and I was the one paying for it?

I replied: [What do you need it for?]

Ethan: [It's urgent, okay? Don't ask.]

Me: [Sorry, I'm broke.]

He replied instantly: [It's only the beginning of the month. How could you be broke already? Stop pretending. I really need it.]

I thought for a moment, then typed: [Alright, I'll lend you the money, but you gotta give me an IOU.]

Over the years, he'd hit me up for money every now and then.

It was never much at a time, but all those bits and pieces added up to over 300 dollars.

He always forgot to pay me back, and I never pushed him about it.

I guessed that was just what you did when you liked someone.

But things had changed.

There was a pause on his end for a few seconds.

Then he sent a voice message, sounding a bit impatient.

"Jessica, seriously? After everything we've been through, you want me to write you an IOU?"

I typed back: [What kind of relationship do we have?]

He didn't reply.

I set my phone face down on the table.

I closed my eyes, lost in thought.

I just couldn't wrap my head around why Ethan would fall for Lily Winters.

Lily and I were roommates back in high school.

We clicked instantly and became best friends.

I first introduced them to each other during winter break in our tenth-grade year.

Ethan came over to help me pack up my things.

That day, Lily just said hi and took off.

During all three years of high school, they hardly ever crossed paths.

When it was time to pick colleges, the three of us all chose schools in the same city.

Since my grades were better, I got into Brookfield University, while Ethan and Lily ended up at Brookfield State College, right next door.

Back then, I teased Ethan, telling him to keep an eye on Lily.

Could it really be just because of that?

Did he really listen to me, started taking care of her, and then caught feelings?

Wait, no. Ethan said he'd had a crush on her for five years.

Doing the math, that would've been back in our tenth-grade year.

Was it love at first sight?

A wave of bitterness washed over me.

My phone buzzed again.

Both Ethan and Lily had messaged me.

I tapped on Lily's message first.

She texted: "Hey Jess, something came up with my birthday party, so let's move it to Sunday, okay?"

My fingers hovered over the screen.

I texted her: [Is something up? Got plans that day?]

She: [Yeah, something came up.]

Something came up...

I wondered if she was going out with Ethan.

I didn't ask any more questions and just replied: [Okay.]

Then I switched over to Ethan's chat.

After grumbling a bit, he agreed to write the IOU and asked me out: [Let's grab dinner tonight. I'll give it to you in person.]

I asked: [Sure, where to?]

He: [BBQ at our usual spot.]

I stared at his last message.

Back then, seeing "our usual spot" always made me feel warm inside.

Now, it just felt bitter.

Chapter 1

Back when I was dead broke, I started moonlighting as a relationship coach on a secondhand marketplace app.

My childhood friend, Ethan Carter, ended up being my very first client.

He had no idea it was me behind the screen.

His first message after placing the order was:

My heart started pounding as I read his message.

I was the girl he'd known the longest.

And yeah, there really was someone chasing after me lately.

So, was he talking about me?

With a bit of selfish hope mixed in, I encouraged him to take the leap and tell the girl how he felt.

He agreed to follow my advice.

He even mentioned that her birthday was in two days, which sounded like the perfect opportunity.

My fingers froze over the keyboard.

Wait, two days from now?

Hold on, wasn't that my bestie's birthday?

*****

I spaced out for a second.

My phone kept buzzing.

He messaged again: [There's a rooftop restaurant downtown with a killer view of the city lights. I'm planning to take her there for dinner and confess my feelings.]

The restaurant he mentioned was called Cloud Nine.

I was the one who recommended it to him.

I told him the night view was gorgeous, and that I'd definitely go there someday when I could afford it.

Back then, he scoffed and said, "A meal there costs over 300 dollars? Only suckers would go there."

Who would've thought he'd end up being the sucker himself so quickly?

I gave a wry smile and typed: [Congrats. Isn't that place super expensive?]

His reply came quick and cheerful. [Confession's gotta be formal, you know.]

We were still chatting when my phone buzzed with a new WhatsApp message.

It was a message from Ethan.

Ethan: [Can you lend me 300 dollars? I'll pay you back next month.]

I stared at the message.

I couldn't help but laugh in exasperation.

I couldn't help but think: wait, so he was confessing to someone and I was the one paying for it?

I replied: [What do you need it for?]

Ethan: [It's urgent, okay? Don't ask.]

Me: [Sorry, I'm broke.]

He replied instantly: [It's only the beginning of the month. How could you be broke already? Stop pretending. I really need it.]

I thought for a moment, then typed: [Alright, I'll lend you the money, but you gotta give me an IOU.]

Over the years, he'd hit me up for money every now and then.

It was never much at a time, but all those bits and pieces added up to over 300 dollars.

He always forgot to pay me back, and I never pushed him about it.

I guessed that was just what you did when you liked someone.

But things had changed.

There was a pause on his end for a few seconds.

Then he sent a voice message, sounding a bit impatient.

"Jessica, seriously? After everything we've been through, you want me to write you an IOU?"

I typed back: [What kind of relationship do we have?]

He didn't reply.

I set my phone face down on the table.

I closed my eyes, lost in thought.

I just couldn't wrap my head around why Ethan would fall for Lily Winters.

Lily and I were roommates back in high school.

We clicked instantly and became best friends.

I first introduced them to each other during winter break in our tenth-grade year.

Ethan came over to help me pack up my things.

That day, Lily just said hi and took off.

During all three years of high school, they hardly ever crossed paths.

When it was time to pick colleges, the three of us all chose schools in the same city.

Since my grades were better, I got into Brookfield University, while Ethan and Lily ended up at Brookfield State College, right next door.

Back then, I teased Ethan, telling him to keep an eye on Lily.

Could it really be just because of that?

Did he really listen to me, started taking care of her, and then caught feelings?

Wait, no. Ethan said he'd had a crush on her for five years.

Doing the math, that would've been back in our tenth-grade year.

Was it love at first sight?

A wave of bitterness washed over me.

My phone buzzed again.

Both Ethan and Lily had messaged me.

I tapped on Lily's message first.

She texted: "Hey Jess, something came up with my birthday party, so let's move it to Sunday, okay?"

My fingers hovered over the screen.

I texted her: [Is something up? Got plans that day?]

She: [Yeah, something came up.]

Something came up...

I wondered if she was going out with Ethan.

I didn't ask any more questions and just replied: [Okay.]

Then I switched over to Ethan's chat.

After grumbling a bit, he agreed to write the IOU and asked me out: [Let's grab dinner tonight. I'll give it to you in person.]

I asked: [Sure, where to?]

He: [BBQ at our usual spot.]

I stared at his last message.

Back then, seeing "our usual spot" always made me feel warm inside.

Now, it just felt bitter.