Computing the diameter of a graph, i.e. the largest distance, is a fundamental problem that is central in fine-grained complexity. In undirected graphs, the Strong Exponential Time Hypothesis (SETH) yields a lower bound on the time vs. approximation trade-off that is quite close to the upper bounds. In \emph{directed} graphs, however, where only some of the upper bounds apply, much larger gaps remain. Since $d(u,v)$ may not be the same as $d(v,u)$, there are multiple ways to define the problem, the two most natural being the \emph{(one-way) diameter} ($\max_{(u,v)} d(u,v)$) and the \emph{roundtrip diameter} ($\max_{u,v} d(u,v)+d(v,u)$). In this paper we make progress on the outstanding open question for each of them. -- We design the first algorithm for diameter in sparse directed graphs to achieve $n^{1.5-\varepsilon}$ time with an approximation factor better than $2$. The new upper bound trade-off makes the directed case appear more similar to the undirected case. Notably, this is the first algorithm for diameter in sparse graphs that benefits from fast matrix multiplication. -- We design new hardness reductions separating roundtrip diameter from directed and undirected diameter. In particular, a $1.5$-approximation in subquadratic time would refute the All-Nodes $k$-Cycle hypothesis, and any $(2-\varepsilon)$-approximation would imply a breakthrough algorithm for approximate $\ell_{\infty}$-Closest-Pair. Notably, these are the first conditional lower bounds for diameter that are not based on SETH.