I have a friend who doesnt feel regret when they sin and theyre having trouble getting that regret. How can they be more regretful after sinning?

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You can share these points with them.

1- Realize whom you have sinned against. Allah has been so kind to you and you still sin against him? You are sinning against the king of the universe. That’s big.

2- Remember the Prophet and the Imams witness your deeds. When you sin you disappoint them.

3- Sins can take away your faith, and one can die an unbeliever God-forbid. They make Shaytan more empowered over us.