Summary: Rukia learns that she has to go on a series of dates set up by a matchmaker and one of her friends. Will she find the right man on all the various dates? Or will she be left wondering if love is really worth all the trouble, especially when you have a lot of male friends?

Disclaimer: I do not own Bleach.

Prologue

Byakuya walked into his office where Rukia waited semi-patiently for him. She was too busy pulling at her gloves as her brother's spiritual pressure froze her in place. She dropped her hands quickly by her side and straightened up her back as she became a perfect example of a poised princess. Her violet eyes widened as she noticed her normally straight laced brother had a bottle of sake in his hands. She watched him as he took two cups from a hidden location behind some books in his extensive library. Slowly, Byakuya poured Rukia a drink and handed the cup to her. The amber liquid represented something was wrong. Byakuya normally would pour her tea, but this was sake. This conversation was not going to be good!

"Please take a sip of your drink, Rukia." Byakuya said with a strained voice. He was dreading having to place this burden on her, but he was not remarrying again. He would not tarnish Hisana's memory with a less inferior woman. Amid his inner turmoil, he watched as Rukia quietly drink her sake before he told his beloved sister the truth behind his numerous meetings lately. With an inaudible sigh, Byakuya captured Rukia's attention because the great clan leader never sighed.

"Rukia, the Kuchiki elders have decided that you must marry."

His words froze her in place. No! They can't make me… It's too soon in my life! I just became a lieutenant. What if the man they pair me with won't let me be a captain? What if I hate the man?

Byakuya watched the various thoughts flicker across Rukia's face. Her normal Kuchiki composer was still present, but he could read her like a book. She was upset and in shock. Could you really blame her? No… You couldn't because you refused to marry yourself.

"When…" Her voice squeaked as she began to ask when the torture was going to start, but she refrained from phrasing her wording like that as her throat felt like it was closing up. She refilled her glass with more sake as she drank deeply. With a deep breath, she began to finish her sentence. "When shall the matchmaking begin?"

"A week from today. You will begin to go on dates chosen from the Soul Society and possibly the human world. Lieutenant Masumoto suggested that you be given the option of possibly choosing a friend."

"Rangiku knows about all this?" Rukia asked in shock. Her brother never involved outsiders in clan business.

"She is your liaison with the matchmaker. Since I could not stall the elders any longer, I thought that you would appreciate having a friend lend a hand."

"But brother…"

Byakuya held his sister's glaze for a moment. "I tried to give you more time, but they are insistent. You will attend your scheduled dates and eventually chose a husband, Rukia. I was at least able to grant you the choice of choosing your husband out of the various candidates. You are a Kuchiki; therefore, you must do what is expected of you."

Rukia rose from her chair and bowed to her brother. "Thank you, brother. May I be excused?"

He nodded his head. Byakuya watched as Rukia left with determination and sadness in her eyes. Do not worry, Rukia. I will make sure you are happy in the end.

(A/N): Sorry that Byakuya may be a little OOC for a bit, but he does love Rukia even though he doesn't show it often. Rukia may be a little OOC at times, but it will be used to fit the story lines. If there is a pairing/dater that you hate, please be nice since the main pairing will not be till the end so expect random dates from captains and lieutenants for sure. If you are curious about a pair PM me. I will try to update weekly. Some of the chapters are going to be short just for quicker updates! Thanks for reading y'all! I hope you enjoyed the story!