Anakin had noticed the behavior shortly after he had stopped staying with his old Master. During late nights, he would be walking to the landing platform; weaving through the minimum traffic of the Jedi temple, he would see them.
His master's room was at the end of the hall near the hangar, and though he didn't exactly try to listen, it was sometimes hard to miss the giggling that would come through the door. And it was impossible to miss the times that the door would open and a woman he had never seen before would come out, clothes pulled on haphazardly or hair in a mussed up state. They weren't prostitutes, in fact, he could have sworn that once he saw the woman who was the only human waitress at Dex's diner emerge form Obi-Wan's room, a wild smile on her face.
They always smiled at him; knowing he could tell what had happened but not knowing his connection to the man in a similar state on the other side of the door. They would walk to the landing platforms as well, boarding what were usually two person speeders, or calling for the air taxis that would take them home, paying with what Anakin could see were Obi-Wan's credits. He had to keep himself from laughing at that; of course Obi-Wan would pay for his dates a ride home, he was always the resolute gentleman.
But now, after seeing this sort of behavior for weeks, Anakin couldn't push it out of his mind as he usually did when he was with Obi-Wan, who was sitting across from him, reading a data pad and stabbing at bits of a salad. "Is something on your mind, Anakin?" His old master looked up through his now short hair, his eyebrows cocked.
"Just the war." Obi-Wan narrowed his eyes, turning off the datapad.
"You usually don't smile like that when thinking about battle strategy." Anakin couldn't help the smile, looking down at the soup he hadn't been able to eat for trying not to laugh. "Out with it."
"I just met someone interesting last night."
"And who might that be?" His old master was suspicious, probably with good reason considering the idiotic grin stretched across his face.
"Well, you see, I was going to the hangar last night, to check on my ship." Obi-Wan said nothing, eating another berry off the top of his salad. Anakin had always been amazed at his master's ability to eat salads with no dressing, but the man seemed to get some genuine enjoyment out of it, so he just shook his head with a small grimace. "And there was a woman who I had never seen before in the hallway."
"Alright?" Anakin smirked, Obi-Wan was good. His face gave away nothing, no subtle shifts in his face or body.
"So I spoke with her, thinking she might be lost." Anakin took a sip of water, watching for Obi-Wan to give something away, but he only took a bit of the leaves decorating his plate. "She wasn't. She said she had instead enjoyed a terrific evening with a Jedi Master."
Obi-Wan said nothing, but Anakin noticed that his next blink took a bit longer than the ones before. "I asked her what exactly that meant, and she was quite descriptive."
Then Obi-Wan couldn't help himself, he choked on his food, trying to cover it up as a cough. "What," he cleared his throat. "What do you mean?"
"You know, nice dinner, nice conversation, some wine…" He dropped his voice down. "A good time in his apartment."
"Oh." Obi-Wan had nothing to say for the first time since Anakin had known him.
"I made sure she got a cab, it seemed the least I could do."
"What do you mean by that?" Obi-Wan's face was burning under his beard, his eyes wide. But the man stood, rearranging his lunch tray to take it to the garbage, having a meeting he was already a little late for. But he clapped Obi-Wan on the shoulder, dropping his voice to a low whisper.
"For helping bring a smile to your serious face, Obi-Wan."
"Anakin!" The older man nearly shouted, Anakin walking away, laughing to himself as half the cafeteria turned to Obi-Wan, who was burning with embarrassment at the end of the table they had shared.
It was fun to tease Obi-Wan; and Anakin decided that as long as he never saw Padme leaving the Jedi Master's room, he could be happy that his master was enjoying himself.