Summary: Rapunzel unexpectedly learns what the expression "not bad with the ladies" really means when it comes to Eugene.

A/N: Inspired by all those E-harmony "Wingman" banner ads that popped up awhile ago whenever I came to this site. For some reason, this was a struggle for me to write, so let me know what you think!

Disclaimer: Don't own Tangled.

"He looks so sad, Eugene."

"Maybe he just wants to be left alone."

It was a lively night at the finest tavern in the kingdom, where the Princess of Corona, her future Prince Consort, and their pub thug friends gathered to hear Hookhand's newest performance. A jovial medley filled the room intermingled with the sounds of rowdy conversation and laughter amongst the patrons. After enjoying a drink or two, Rapunzel lazily rested her head on Eugene's shoulder when someone else caught her attention. And the last thing Eugene wanted was for Rapunzel to be overly concerned about someone other than him.

"No, I think something's wrong." Rapunzel wandered over to where Big Nose had been sitting for the past hour, forcing Eugene to reluctantly follow.

"Hi Big Nose, mind if I join you?"

"Of course not, Princess," he replied with a rueful grin.

"Are you alright?"

He shrugged and further sunk into his square shoulders.

"Can I help?" Rapunzel persisted.

Big Nose sighed. "Well…there's this girl." He motioned in the direction of a striking redhead with wayward curls at the far end of the bar. "Over there. She's Shorty's daughter."

"Shorty's daughter!" exclaimed Rapunzel and Eugene in unison.

"She's here for a visit...and I...I sort of taken a fancy to her," Big Nose finished under his breath.

"She's pretty...," said Rapunzel.

"Tall," Eugene interjected. "Who would've guessed?"

"Probably takes after her mother. Shorty has a thing for tall women," Big Nose explained.

"Why don't you go talk to her?" Rapunzel suggested.

Shaking his head defeatedly, Big Nose stared at the bar counter. "It's not that easy. I get nervous...and clam up around a pretty little lady."

Rapunzel's eyes widened as she thought of a way to help her friend. "Eugene can help. He's not bad with the ladies. Isn't that right, Eugene?"

Eugene's mouth slacked open and he darted a slight glare at Rapunzel. "I don't think that's such a good idea."

"You told me so Eugene. Can you give Big Nose some advice?"

The two men exchanged glances, each silently contemplating the proposal. Big Nose was skeptical, but he was out of ideas himself. "Alright, Rider, I'm all ears. Whaddya got?"

"Fine." Eugene rubbed his goatee as he reflected, "Well, there's an art to seduction. The way you carry yourself, exude confidence, be smooth as fine wine. Then there are the physical traits. Great hair, great smile, perfect nose." Eugene surveyed Big Nose's visage and realized maybe that wasn't the best feature to highlight. "Hmm, alright let's try to play up your other, um, qualities? What about your name?"

"Huh? It's Big Nose, wiseguy!"

"No, I mean your real name. Everyone's got one, right? We need something that doesn't draw so much attention to your, um, less striking features."

"...It's Jeffrey."

"Oh, that's a lovely name," chimed in Rapunzel.

"Much better," Eugene agreed. "Okay, now what's your modus operandi?"

"Huh? What's that? English, Rider."

"You know, your MO, the main move to make the ladies swoon and fall at your feet?" Eugene replied rather tersely.

"What do you mean? Like your smolder?"

"Oh, teach him your smolder, Eugene," Rapunzel piped up.

"I don't think so. Not everyone can pull it off. Besides, there's a fine line between smoldering and looking like someone stomped on your foot." And frankly, Eugene was out of practice since the smolder never worked on Rapunzel. She fell for his vulnerable, puppy-dog-eyed look, which was never going to be put on display in front of another man. Nope, not going to happen.

Eugene groaned inwardly knowing this wasn't getting anywhere. Another approach was needed. "Tell you what; I'll be your wingman for the night."

"What's a wingman?" Rapunzel asked.

Turning to Big Nose, Eugene explained, "It's simple really: I'll approach your girl, talk you up, and give you a signal if she's game. Then you come over and she'll already be falling at your feet."

"You sure about this, Rider?" But at this point, Big Nose was willing to try anything.

"Of course. Trust me."

Rapunzel gave Big Nose her most reassuring nod. She watched from the edge of her seat as Eugene casually sauntered over and approached the redhead in question. He gave the girl his most winning smile. He was a charmer indeed and Rapunzel couldn't help but admire him from her perch. He introduced himself and the girl blushed. Before she even realized, Rapunzel was engrossed in the cascade of events unfolding before her eyes, but her initial excitement rapidly spiraled into an unexplained trepidation. Eugene said something else and the girl giggled. Wait, did she just bat her eyelashes at him? Did she just toss her hair? Did she just playfully swat at his chest? And did she just place her hand on Eugene's forearm? That was quite enough! With a swish of her skirts, Rapunzel was spurred to action. She leapt off her stool, almost knocking it over, and grabbed Big Nose by the arm.

"What about the signal…," Big Nose muttered, only to be abruptly pulled by Rapunzel to where Eugene was standing.

"Pardon me, miss. This is Big Nos-...ah, I mean Jeffrey. He's really nice and he would like to talk to you," Rapunzel blurted out.

Big Nose managed a feeble, "Hiya," before Rapunzel clasped both of her hands firmly on Eugene's forearm and tugged him towards the entrance of the tavern. "Eugene, let's head back."

"Rapunzel, wait. What's going on? Hookhand's not even finished with his song."

She ignored his comment and continued to pull him outside to where Max was waiting at a nearby tree. The brisk night air was exactly what she needed to clear her thoughts and sort through the muddle and confusion of what had just happened.

Stopping her in her tracks, Eugene gently turned her around by the shoulders to face him. Concern furrowed his brows. It was unlike Rapunzel to leave so brusquely without saying good-bye to the pub thugs. "Hey, are you alright?"

"Yes...I thought it would be best to leave them alone...that's all." She bit her lower lip, crossing her arms under her chest.

She was a horrible liar and he saw right through it. He searched her eyes and tenderly took both of her hands into his own, slowly peeling back her defenses. "What happened in there?" he whispered.

Under his intense gaze, she caved. "I didn't like…how she was...acting around you."

His eyes closed shut for a split second as realization hit him like a stone wall. "Rapunzel, I was only telling her about Big Nose. Did I do something wrong?"

She looked away to avert meeting his eyes, trying to make sense of her flurry of emotions. She knew how handsome Eugene was and the stolen glances he got from other women, but something about tonight hit a nerve.

"I wasn't even using the smolder," he attempted to break the tension somehow.

"That's the thing. You were just being you. It works better than the smolder…and not just on me," she finished meekly.

"Rapunzel-..."

"I've seen how other women smile at you at the castle or when we're out in town," she cut him off.

"And all I do is smile back politely." He brought his thumb up to gently lift her chin, forcing her to meet his eyes. "I'm sorry. You have nothing to worry about. I love you."

"I know," she said shyly blinking back a faint sparkle of tears that threatened to trace her lashes.

The uncertainty in her voice left him unconvinced and in that moment his heart gave one sickening lurch. Never would he want to hurt her even if it was unintentional. The truth was no other women, nor riches, nothing held his attention the way she did. But words seemed to elude him. He had to show her.

He cupped her cheeks with his hands and gently moved a strand of her hair from her face. Searching her eyes, he silently pleaded, longing to set things right. He moved in closer until their foreheads touched and he could feel her breath. He leaned in, but hesitated, until he got her permission when she closed her eyes and stood firmly in place, unflinching. Then he kissed her. Slowly and tenderly, then desperately. He poured everything he had into her. He wanted her to know she was the only one that mattered.

She responded with equal desperation, letting the rawness of her emotions consume them both. She took everything she could, and in their kiss, she knew. She knew that he was hers and hers alone. And any remaining doubt she had faded into the night air.

He let her be the first to pull apart, and held her tightly until she was ready to let go. "So are we still heading back?"

"Yes and no," she replied coyly.

"Oh really, so where are we going?"

"Somewhere where you can only smolder at me."

"I thought the smolder didn't work on you?"

Her eyes danced mischieviously. "Well, I changed my mind." The Flynn Rider smolder was ineffective, but the Eugene charm would get her every time.