Ultimately, she decided to go for it with Jack which really destroyed sex for her because her father died the same night. In the pilot episode, Grace starts wearing a purity ring given to her by her parent's to show that she won't have sex until she is married.
After catching Jack with fellow student Adrian, Grace breaks up with him, but they soon get back together. Then Jack ends things with Grace out of jealousy and even claims that he only dated her because his step-father wanted him to. Grace and Ricky end up dating, but Grace breaks up with him soon after when she discovers that he's been sleeping with Adrian. Grace starts to date Grant, who was previously involved with Ashley Juergens although they broke up because Ashley had a sexual interest in Ricky. She wants to fool around, but he refuses to after Grant's mom threatens . Grace goes to Africa and cheats on her then-boyfriend Grant with a college boy (that she slept with) named Daniel.
Grace's mother finds out that Marshall cheated on her with a women in the Vatican and he fathered a boy named Jacob who is only a couple of years younger than Grace. Grace ultimately skipped med camp that year and decided to move in with her best friend Adrian. When Jack and Grace are on a break, Jack sleeps with Clementine, Ricky's friend from a group foster home they both spent time in. In the series finale Thank You and Goodbye, Grace and Jack decide to end their engagement, but they stay friends.
During the beginning of the first season, Grace wears traditionally pink and wholesome clothing. She thinks she killed her father since before he boarded a plane to Africa they had an argument about Grace having sex with Jack. Although, Ricky and Grace, I think, has one of the most sexual moments on the show (him licking the cookie dough off her fingers ) I don't think these two ever really stood a chance to actually become something.

I hate that they forgot about them though because I've always thought they could be real friends.
The whole town's thrown into a tizzy when good girl Grace is caught on tape doing something bad. While the Bowmans are trying to figure out how to punish Grace for going behind their backs, the Juergens see Ashley suddenly turn into a good girl, which raises red flags. Looks like Amy can't keep her big secret under wraps much longer, because by now the whole school knows she slept with Ricky … and the Bowmans know she's pregnant. Meanwhile, Grace decides to punish herself by quitting the cheerleading squad, and to punish Jack by taking Ricky to church. According to The Secret Diary of Ashley Juergens, this episode takes place from September 20-21, 2008. However, the date of September 20 is a continuity error, because the beginning of the episode takes place on a school day, while September 20, 2008 was actually a Saturday. Tammy is a supporting character in The Secret Life of the American Teenager, introduced in Season 1. Then, he decides that he loves Grace too much to lose her again, so he goes back to being a Christian which helps his college football team's notoriety. It's really obvious with the little things they say, how Jack comes in just about every time there's a conversation in Grace's kitchen (Creeper! One-he was still sleeping with Adrian while with her, Two- he didn't really put in any effort with her, Three-he had all of this drama combined with Amy and with Adrian. I liked that he was the only one that could talk some sense into her to get out of the car at her dad's funeral because he knew if he didn't get her out, she would regret it.
When two guys harass her on a street corner after dark (following another of her secret meetings with Jack, of course), Grace rises to the occasion and threatens them with a broken beer bottle, street-fighter-style. As does a certain piece of gossip dad hears at the store, about one of his girls having sex (wonder who THAT could be?).

Even AMY is ready to spill the beans, but her parents don't believe her when she confesses she's been having sex. September 21 is a Sunday, though, and the episode does end on a Sunday which is canonically correct. Who is struggling to control his sexual feelings towards Grace, and their shared christian beliefs. She admits to Adrian that she was "curious." They kiss to quell their curiosity which scares Grace and she runs back to Christianity.
She tells Jack that she wants to get together with him, but only in a monogamous relationship. All of a sudden, Ricky jumps in to save her, and both of them are caught on camera … and Ricky's not wearing a shirt.
Maybe they're just too distracted, what with Anne being so busy worrying about whether or not GEORGE is having sex — with another woman. While those four are going at it, Ben and Amy are working out some serious relationship issues—especially after Ben's dad brings up the suspicion that Amy might be pregnant.
Plus, they keep on discreetly showing their jealousy towards eachother's new relationships. I think with Bob coming it gave him a reason to break up with her because he never was true to her anyway.
He didn't even want her to know about Bob getting sent back to prison so in away, Bob coming, gave him an out to his and Grace's relationship without necessarily being the BAD guy about it, you know.

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