Safe to say, Tom was already looking forward to their second date after the last one had gone extremely well, not expecting it to go so perfectly. After asking his friend to sit for his daughter that night, he made his way to grab his jacket and check the mirror one last time and ensure his makeup was still in place before he grabbed the box of chocolates off the table that he had purchased for Felicity. It had been a long time since Tom had done anything like this and he wanted it to be perfect, whatever was to come. Grabbing the keys to his car, he hurried out the door, realizing he might be running a little late rather than early if he wasn’t careful; he just had to double-check that Penelope would be alright. Of course, he had no real reason to worry; she was in good hands with his friend. Making his way out to his car and hopping inside, he started the engine- once, twice- until it finally roared to life and began to drive smoothly down the road. He had managed to specify later nothing too formal, no dresses needed, she could dress whatever way she liked- he certainly had. Leather jacket and a tank top to keep himself cool underneath it, and a faint smile on his face as the radio played in the background in a soft tone. Being that Crownsville was small, it didn’t take him long to arrive at her place, remembering to grab the box of chocolates from his seat when he had parked the car and honking his horn to signify his arrival just to be a brat, smirking to himself as he did so before climbing out. Heading for the door, he easily took the two steps up, thanking a god he didn’t believe in for blessing him with long legs in spite of being only five-foot-four, rapping his knuckles on the door after a moment and humming to himself, pulling the guitar he had grabbed at the last second from his shoulder, holding the box behind his back. The guitar was, on the other hand, too difficult to hide. Offering her a polite smile when the door opened, he dipped his head before flicking his red hair out of his face. “Your date, m’lady,” he teased, holding out the guitar for her immediately, “There’s my peace offering for you tonight, and uh- shit- these.” Producing the box from behind his back, he held it out to her, smirking. “I thought I’d make a good fucking impression at the door,” he offered as he took a step toward her, planting a brief kiss to her cheek politely.