Ted wasn't exactly a ladies' man. He had once had a wife. Then he'd cheated on that wife with a lot of pretty little things. He hadn't considered the consequences until it was way too late.
"Take her on a date." He offered simply. "Let her know you like her. It's not that complicated."
He didn't mean to be rude or anything like that. It was just one man telling another man that things didn't have to be so hard.
"As for the other one," Ted shrugged. "If you don't feel it, you don't, right? It might hurt her feelings, but what are you going to do, fake it?" He wasn't even going to touch the being in the future or past of anything thing. It was a part of the City's rules that he wasn't quite knowledgeable about yet.
He leaned back in the seat and considered for a moment. "It sort of sounds to me like you don't have a lot of confidence in yourself when it comes to your social life. Which is odd, considering you're a doctor and must have a lot of confidence there, you have to." Ted looked at Simon. "So what's the problem? Where does the disconnect come?"