She Dressed Ugly to Ruin Her Father’s Visit—But He Was the Millionaire She Had Always Wanted

The outfit was the perfect sabotage: an old oversized hoodie, faded plaid pajama pants, flip-flops worn with socks because there seemed to be no reason not to make the disaster complete, hair pulled up like a bird’s nest, her grandmother’s huge glasses, and no makeup. She had chosen every detail with care. It was supposed to ruin the arranged meeting her father had set up without consulting her.

She walked down the stairs proud of her fashion horror masterpiece.

Then she saw him in the living room.

Theodore Ashford.

Her childhood crush. The boy from the almost kiss at the pool. The millionaire she had secretly loved for 9 years. He was standing there in her parents’ living room, looking at her as if asking what had happened to her.

Clare literally fell on the floor in shock.

It was, by any possible measure, the best first reunion imaginable.

Her phone had buzzed in her hand earlier while she stared at her closet like it was her worst enemy. On the other end of the line, her best friend was already laughing before Clare had even revealed what her father had done.

“Let me guess,” her friend said. “Your dad set up another arranged date without asking you.”

“Third one this month,” Clare grumbled, throwing herself onto the bed. “He won’t give up. Clare needs a good man. Clare needs to get married. Clare is getting old. I’m 24 years old.”

“And what are you going to do this time?”

An evil smile formed on Clare’s lips.

“I’m going to dress so ugly that the guy will run away. Then my dad will finally stop trying to push me toward any rich single guy.”

“You’re diabolical. I love it.”

After hanging up, Clare got up with purpose. Operation Horrible Outfit was officially underway. She opened the most forgotten drawers, searching for every piece of clothing relegated to fashion exile for good reason. The oversized hoodie she used for sleeping. The old, faded plaid pajama pants that should have become a cleaning rag. Flip-flops with white socks, because if she was going to do it, it should be memorable.

She pulled her hair into a shapeless bun, grabbed her grandmother’s huge 1980s-style glasses, and put on a cream so light she looked like a Victorian ghost.

When she looked at herself in the mirror, she smiled, satisfied.

It was a horror masterpiece. No man would want to see her again after that first impression.

She went down the stairs with all the confidence of someone ridiculous but proud of it. Each step was a declaration of war against her father’s matrimonial plans. She could hear voices in the living room, her father talking to the poor man summoned for the awkward meeting.

“Clare, finally. Come meet—”

She turned the corner, and the world stopped spinning.

Theodore Ashford stood there in an expensive casual suit. He was taller than she remembered, broader in the shoulders, with a commanding presence. Those blue eyes that had haunted her dreams for 9 years were fixed on her.

It could not be him.

Not now. Especially not while she was dressed like that.

Her legs forgot how to work. The air disappeared from her lungs. Her traitorous body decided the best reaction was to trip on the last step.

She fell on her butt. One flip-flop flew to one side, her grandmother’s glasses to the other.

The silence was so absolute she could hear her heart exploding with shame.

“Are you okay?”

His voice, deeper than she remembered, cut through the silence. He ran to her, strong hands gripping her arms and lifting her with a gentleness that contrasted with the strength she felt in his fingers.

Clare could not look at him. Her face was burning.

“I’m fine. Just tripped.”

“Clare,” her father said sharply. “This is Theodore Ashford. The Ashfords’ son. You’ve known each other since you were kids.”

“I remember.”

She remembered every torturous second of following that man like a lost puppy.

“Clare Montgomery,” Theo said close to her, still holding her arm. “Wow. You’ve grown up.”

Grown up. He said grown up while she looked like a lost homeless person. The irony was brutal.

“Clare Elizabeth Montgomery,” her mother called from the kitchen. “What are you wearing?”

“Comfortable clothes.”

Owen appeared laughing.

“Clare, you look like you lost a bet.”

Theo was still holding her arm. Clare felt the warmth of his hand through the hoodie, each finger marking her skin. When she gathered the courage to look up, those blue eyes were studying her with an intensity that made her stomach flip.

“You dressed like this on purpose?” he asked quietly, only for her to hear, amusement in his voice.

“Maybe.”

A devastating smile formed on his lips.

“To scare me away?”

“I didn’t know it was you.”

“So if it had been someone else, you would have scared him away. But with me—”

He left the sentence hanging, provocative.

Clare had no answer while he was that close, looking at her like that.

“I need to change clothes. Excuse me.”

She ran upstairs, hearing Owen still laughing, her father asking what had gotten into her, and her mother murmuring about embarrassment. But the only voice echoing in Clare’s mind was Theo saying her name as if it was the first time he was truly seeing her.

She locked her bedroom door and leaned against it, breathing deeply while trying to control the trembling in her hands. Her heart beat irregularly. The vertigo she had always felt around him had returned in full force.

“Okay, Clare,” she told herself. “You’re not the little girl he used to tease anymore. You’re Clare Montgomery, successful designer, independent, and you are not going to melt at his feet just because he came back handsome and powerful.”

She grabbed her phone and called her friend.

“So,” Clare said. “It was Theo.”

“Theo? Your crush from—”

“Was. Past tense. I got over him years ago.”

“You got over him.”

“I’m trying to get over him again starting now. Urgently.”

“Is he good-looking?”

Clare closed her eyes, seeing those blue eyes, that jaw, that smile.

“Absurdly good-looking.”

“And you wearing flip-flops with socks and looking like a ghost.”

Her friend laughed.

“Perfect.”

“But you know what? Screw him. I’m not going to make it easy just because he came back after 9 years. I’m not going to be that girl again.”

“That’s my Clare.”

Clare hung up and went to the closet, choosing carefully. She was not going to dress up too much, but she was also not going to let that horrible impression be the final image of her.

While she brushed her hair, memories invaded her mind.

The flashback was instant. Clare at 13, with braces and huge glasses. Too skinny, awkward, following Theo and Owen like a lost puppy. Theo at 17, already too handsome and popular, calling her Glasses, Pest, and Matchstick.

“When are you going to grow up, pest?” he would say, messing up her hair.

Clare would laugh because at least he paid attention, even if it was to tease her.

But she also remembered how he defended her when others tried to tease her.

“Only I can tease my annoying little sister,” he would say, with a strange and possessive protection.

She shook her head. He had teased her, made her cry in hiding more times than she could count. And now he came back expecting what, exactly?

30 minutes later, Clare went downstairs again wearing a navy blue dress that was casual but elegant, her hair loose in natural waves, light but strategic makeup, and low heels that gave her confidence. Theo was talking to her father about business. When he saw her, the conversation died.

He stood slowly, and his blue eyes traveled over every inch of her with an intensity that made her skin heat.

“Wow,” was all he said.

But the word came out loaded with weight.

“Sorry about the dramatic entrance earlier,” Clare said. “It wasn’t the best first impression.”

“You don’t need to apologize. No one can deny it was memorable.”

She crossed her arms, creating a physical barrier even with several feet between them.

“So, Theodore. I heard you came back from London.”

Something passed over his face when he heard his full name.

“I came back a few months ago to take over the family business.”

“That’s good. My parents will love to catch up,” she said, grabbing her purse. “But I have an appointment, and I need to leave now.”

“But we barely talked.”

“I have a lunch scheduled. I can’t cancel. It would be rude.”

“Clare,” her father protested. “Theodore came to see you.”

“And I appreciate the visit. Theodore, it was good to see you after so many years.”

A polite, generic smile. Then she turned to leave.

“Wait. Can we schedule another day to catch up?”

Clare stopped and looked over her shoulder. He was there, too handsome, with those eyes begging for something she was not ready to give.

“Maybe. If I have time in my schedule.”

She saw the shock pass over his face. Women probably did not say maybe to Theodore Ashford.

“Okay. Can I call you?”

“Owen has my number. You can ask him.”

Then she left, feeling the weight of his eyes on her back until she got into the car. Only when she was safe inside the vehicle, away from those eyes that saw too much, did she allow her body to shake. Her hands gripped the steering wheel while she tried to control her uneven breathing.

Theo stood staring at the door Clare had left through. The sound of her car driving away echoed through the house, and something strange settled in his chest.

“Dude,” Owen said, appearing with a mocking smile. “She completely dismissed you.”

Theo turned to his friend, processing what had happened.

“She said she has an appointment.”

“What appointment?”

Owen crossed his arms.

“Probably lunch with Lucas.”

The tightness in Theo’s chest grew stronger.

“Who?”

“Lucas Reed. The guy who’s been hitting on my sister for months. She’s seriously considering him.”

“Considering as in—”

“As in considering making him her official boyfriend soon, if she agrees to really go out with him. He’s good. Treats her like a queen. Respects her. Doesn’t disappear for 9 years.”

The jab was direct. Theo deserved it.

“I see.”

Clare’s father appeared.

“Theodore. You were surprised by our Clare, weren’t you? She changed so much. Grew up. Became a beautiful woman. Successful. Independent.”

“Very much,” Theo agreed, but his eyes remained fixed on the door. “She changed a lot.”

The casual restaurant Lucas had chosen was exactly the type of place Clare loved. Nothing pretentious. No waiters in suits. No menus impossible to pronounce. Just good food, a welcoming atmosphere, and company that did not make her feel as if she were constantly being judged.

“You look beautiful today,” Lucas said as soon as he saw her.

His smile was so genuine that Clare managed to relax her shoulders a little, though she had not realized they were tense.

“Thanks, Lucas.”

She smiled back, sliding into the seat across from him and letting the warmth of the restaurant chase away the cold still inside her from that disastrous morning.

He waited until they ordered before leaning slightly forward, his brown eyes full of amused curiosity.

“So, how was the visit your dad set up? Did you manage to scare the poor guy away?”

Clare laughed despite herself, remembering the horrible outfit and the spectacular fall.

“Disastrous. I dressed terribly on purpose and ended up falling on my butt in front of the guy. It was epic in the worst possible way.”

Lucas laughed out loud, that easy, light laugh that always made her feel comfortable.

“Seriously, are you okay? Nothing hurt besides your ego?”

“My ego is destroyed. But yes, physically I’m fine.”

She took a sip of water, trying not to think about how Theo’s hands had felt around her arms. Warm, firm, completely devastating.

“And the guy?” Lucas asked. “Did he run away like you planned?”

Clare paused.

A pause that lasted too long.

“Not exactly.”

Lucas tilted his head, noticing her hesitation.

“No?”

“It was Theodore Ashford. I knew him when I was a kid. We grew up together.”

The words came out faster than she intended, as if saying them quickly made the fact less important.

Recognition passed over Lucas’s face immediately.

“Ashford as in the billionaire from Ashford Industries?”

“That Ashford. Yes. Our parents are longtime friends. Owen and he have been best friends forever. We practically grew up together.”

Clare fidgeted with her napkin while talking, avoiding his eyes.

“When you—”

Lucas paused, choosing his words carefully.

“Do you want to see him again?”

Honesty. Lucas deserved honesty.

“I don’t know. It was weird after so many years. He changed. I changed. It’s like we’re strangers who share old memories.”

Lucas nodded slowly, processing. Then he took a deep breath in a way that indicated he was about to say something important.

“Clare, I’ve wanted to ask you something for weeks.”

Her heart gave a small jump.

“What?”

“We’ve been going out a lot as friends, and I really like you. A lot. Would you want to try something official? Like actually dating?”

The surprise was not unpleasant. But it was not the explosive joy a woman should feel when a good and kind man asked her to be his girlfriend.

“Lucas—”

“You don’t have to answer now,” he interrupted gently, taking her hand on the table. “Think about it, okay? No pressure. No rush. Just think about it.”

“I will think about it. I promise.”

And it was true. Lucas deserved for her to think carefully, to give him the real consideration he deserved.

Night had fallen completely when Theo met Owen at the bar they had frequented since college. The place was discreet, far from the spotlight that usually followed the Ashford name, and that was exactly why Theo liked it.

“So,” Theo began as soon as the beer arrived, trying to sound casual and failing miserably. “Tell me about Lucas.”

Owen took a long sip before responding, and the smile on his lips was annoyingly knowing.

“Why the sudden interest?”

“Just curious.”

“Sure you are.”

Owen laughed, unconvinced.

“You like her?”

“I don’t like her. I was just surprised by the change. It’s natural after 9 years without seeing someone.”

Theo drank from his beer, avoiding his friend’s penetrating gaze.

“Dude, Clare isn’t the pest who followed us around like a puppy anymore. She grew up. Became a successful designer with work displayed in galleries. She has her own life, a full schedule, suitors who truly value her.”

Theo felt something uncomfortable twist in his stomach.

“Then Lucas is one of these serious suitors.”

“Very serious. He really likes her. Treats her like a queen. Has been trying to convince her to officially date for months.”

Owen leaned forward, watching Theo with calculated attention.

“Why does that bother you?”

“It doesn’t. Good for her, then.”

The words came out drier than Theo intended.

Owen smiled. He had noticed.

“You’re jealous.”

“I’m not.”

“You are, man. You’re transparent. But be careful, because you treated my sister really badly when we were kids. You teased her nonstop. Made her cry. Treated her like she was invisible.”

Theo ran a hand through his hair, frustrated.

“I was an idiotic teenager. I didn’t know any better.”

“And she remembers that very well. She remembers every tease. Every time you made her feel small and ugly and invisible. So if you want any chance with her, you’re going to have to work hard. Very hard.”

9 years earlier, in the summer at the Ashfords’ coast house, Clare was 15 and had spent the entire year preparing for that summer.

She had finally gotten her braces off, traded the horrible glasses for contact lenses her mother had reluctantly agreed to buy, and her body had finally decided to develop and stop making her look like a matchstick.

When she arrived at the Ashfords’ house that first day, her heart beating fast in her chest, all she could think about was how Theo would see her now. If he would finally really notice her, not as the annoying pest, but as Clare.

Theo had come back from college for the summer. When he saw her for the first time at the pool, he stopped completely.

Clare was getting out of the water, and the simple bikini she had chosen on purpose was not anything special. But the way he looked at her made her stomach do somersaults.

“Who is—” he started to ask Owen, who was beside him.

“It’s Clare, bro. Clare the pest.”

The shock in his voice was unmistakable.

“Don’t call her that anymore. She grew up.”

Clare saw when Theo really looked at her then. His eyes traveled over her face, her body, and back to her face.

“I see that.”

The following days were delicious torture. Clare caught him looking at her when he thought she was not paying attention. The dynamic between them had completely changed. She was no longer the annoying child. She was something else, something that visibly confused him.

Then came the day at the pool.

Clare had gotten out of the water, and Theo was there pretending to read a book, though his eyes lifted every time he thought she did not see. She gathered all the courage she had at 15 and approached.

“Theo, can I ask you something?”

He looked up, and for the first time in her life, she saw nervousness there.

“Sure.”

“Why did you stop teasing me?”

Silence.

Then, quietly, he said, “I don’t know. You changed.”

“Changed how?”

She sat beside him, too close, too brave.

He looked at her, and there was something dangerous in that look.

“You know how, Clare.”

Her heart raced so fast she thought it would jump from her chest.

“I don’t know. Explain it to me.”

He moved closer, and every inch the distance between them decreased made her breathing harder.

“You got beautiful, Clare. Very beautiful. And that’s complicated.”

“Why complicated?” she whispered, hypnotized by his closeness and the heat radiating from his body.

“Because you’re my best friend’s sister. You’re 15, and I’m leaving for college in London next week.”

His voice was hoarse, low, dangerous.

Clare was brave in the way only teenagers in love could be.

“What if I were 18? What if you weren’t leaving?”

“Then maybe.”

He leaned in, his eyes fixed on her lips, and Clare closed her eyes, waiting, wanting, needing.

“Theo, dude, let’s play.”

Owen’s voice exploded out of nowhere, and they pulled apart so fast Clare almost fell off the chair.

“I’m going inside.”

She ran before Theo could see the tears of frustration in her eyes.

After that, Theo avoided her for the rest of the week. Then he left for London and did not come back for 9 whole years.

Clare kept that in her heart: that almost kiss, that almost declaration, and let it turn into a scar.

Theo was alone in his apartment, the conversation with Owen still echoing in his head.

She was not that girl anymore. She had become an amazing woman. And he had been the idiot who teased her, who almost kissed her and ran away like a coward.

Now she had another man. A good man, one who treated her well and did not carry the baggage of 9 years of cruel teasing.

But Theo wanted a chance.

Needed a chance.

He grabbed his phone before he could convince himself otherwise and texted Owen.