Since they’ve gone on their separate paths, she’s been in his thoughts. This shows that he hasn’t truly gotten over here and further supports the idea that both of their current relationships are rebounds.

He asks “why?” because it’s hard to cope with such a distant love, especially if you can’t tell if they love you back.

Elijah knows his Ex is in a relationship, but he also knows that her new man isn’t doing it for her.

She isn’t committed to her new man and, therefore, their relationship isn’t secure at all. If anything, her new man could be her rebound relationship to get over Elijah.

Oh yeah, and his new girl is also a rebound fling that he isn’t fully committed to.

Elijah is caught up in the nostalgia of their relationship and thinks they could still make it work.

If they could put water under the bridge and make it past their past misdemeanors, then Elijah thinks they could be something again

Common says, in a glaringly obvious reference to his relationship with Serena Williams, that when she was playing in the US Open it was the proverbial nail in the coffin that was their relationship.

As the Open is held in August/September, it is clear to see that things grew sour between then and May, which leads into the Winter as referred to later in the song.

With all the different opinions in his mind, Dot doesn’t know which is the right choice, especially because the result will most likely affect his public and private lives in a big way.

When a person gets famous, many people turn on them, making wild accusations about the ideal of “selling out”. Dot seems to know his fans will end up thinking this if he becomes one of those Top 40 rappers, but that they’ll still see through it because they know who he really is.

A kid from the hood hears his brother has been murdered (possibly by the ‘father’ mentioned earlier in the song, to interlink stories, although that doesn’t really matter).

After hearing his brother’s been murdered, instead of grieving, the kid gets a burner, (a handgun), and searches for the person who killed his brother, not caring if he kicks down a few doors on his way.

Wile Out

Here, Dot says that what was once heartfelt (a sincere or deeply honest feeling) is now distrustful, and this makes him question his antics in youth.

This is because he’s a “new man” and now shuns his old ways, as he sees now that they were wrong.

Presumably, I/O’s elder told him to be more patient about the situation, as fame rarely happen over night.

I/O says he has an idea to bring to life, which is parallel to his line earlier in the song

and this dream I’ve got to manifest.

He’s basically responding to the elder and saying that the idea of fame and “making it” is the reason he can’t be patient.

When they were dating she wasn’t serious or supportive enough, not respecting his dream of being a famous singer.

He’s on his way now and doesn’t need the stress of her relationship to affect his life or his art