I believe you have confused Dally with Darry in the second part of your post, but here goes.
Dally comes on to Cherry the only way he knows how--tough, crude and sarcastic. He talks dirty to her, and Cherry eventually throws a soda in his face. However, we find out later that Cherry is actually taken with Dallas Winston, and she says that she could fall in love with him if she saw him again. She likes dangerous types, since her boyfriend is the violent yet handsome Soc, Bob Sheldon. So, though the two never get together, Dally's approach works on Cherry. Needless to say, Dally likes Cherry's spirit and good looks, but he knows better about mixing with a Soc.
Ponyboy is younger and shyer, so he talks to both girls as he would schoolmates. He never forgets that he's a greaser, but he feels important when the girls tell him they feel safe around him. The girls think Pony is cute--and his brother, Sodapop, even cuter--and Cherry decides that she can talk to him about anything. Pony feels the same way about Cherry, and she stands up for Ponyboy later in court. He considers her a friend, though they go back to their own greaser and Soc worlds at the end of the novel.
The sequence that the question is asking about occurs in chapter two. Ponyboy and Johnny meet up with Dally at one of the town's drive-in theaters, and the boys quickly take notice of two attractive Soc girls. The girls are Marcia and Cherry.
Dally doesn't hesitate at all before going up to the two girls. The text says that he took a seat right behind them and started talking "dirty" and loud enough for the girls to hear. It must have been pretty bad because Ponyboy says that he felt his "ears get hot." Ponyboy is in a gang that isn't opposed to "colorful" language, so the fact that Ponyboy finds Dally's words bad enough to be embarrassing means that whatever Dally is saying must be bad.
The girls do an admirable job of ignoring Dally, which just serves to antagonize him. He ups his bravado and attention grabbing behavior by placing his feat on the back of the seats that the girls are sitting in. That finally gets the girls' attention. They turn around and tell Dally to knock it off. They aren't kind about it either, and they let it be known that they aren't surprised at such behavior from a Greaser. Dally just rolls with it and continues to act the tough, bad boy part.
"Oh, my, my"—Dally looked bored—"you've got me scared to death. You ought to see my record sometime, baby." He grinned slyly. "Guess what I've been in for?"
Dally offers the girls a drink and gets a great response in return.
She was mad by then. "I wouldn't drink it if I was starving in the desert. Get lost, hood!"
Dally then leaves; however, he does eventually come back with some Cokes for the girls. He's completely confident in his tough guy persona, his good looks, and the Cokes. Cherry, apparently, still isn't impressed. She takes a Coke and pours it all over Dally and again tells him to get lost. He ignores the request, but is convinced to leave once Johnny speaks up.
Based on this single encounter, it really looks like Dally has zero future chance with Cherry; however, Cherry admits in chapter three that she is definitely attracted to Dally's good looks, self-confidence, and bad boy image.
She looked at me quickly. "I could fall in love with Dallas Winston," she said. "I hope I never see him again, or I will."
Ponyboy's approach to Cherry is completely different. He stays quiet until Cherry talks to him.
"Y'all sit up here with us. You can protect us."
Perhaps it's because Pony knows that he is younger than Cherry, or perhaps it's because he's just not that experienced at talking with girls, but Ponyboy never makes an attempt to "hit on" Cherry or Marcia. He talks to them like people who happen to be female instead of females that are meant to be conquered. Cherry immediately notices this difference and even mentions it.
Johnny grinned. "How come y'all ain't scared of us like you were Dally?"
Cherry sighed. "You two are too sweet to scare anyone. First of all, you didn't join in Dallas's dirty talk, and you made him leave us alone. And when we asked you to sit up here with us, you didn't act like it was an invitation to make out for the night."
Dally's approach treats the girls like they are objects to be won and used, and Cherry firmly rejects him. Ponyboy treats the girls like people, and Cherry and he become close friends that end up sharing a deep, emotional connection.