Suppose $H$ is a subgroup of a group $G$ and both have the same cardinality of $\mathbb{R}$. If $K$ is a countable subgroup of $G$, is it possible that $H$ has not countable index in the subgroup generated by $K$ and $H$?
Clearly $G$ must be not abelian and $HK \neq KH$.
Yes, it's possible. Probably there are easier examples, but here's one. Consider the subgroups of $\mathrm{GL}_2(\mathbb{R})$: \begin{align*} G &= \left\{\begin{pmatrix} a & b\\ 0 & c\end{pmatrix}\mid a,b,c\in \mathbb{R},a\neq 0,c\neq 0\right\}\\ H &= \left\{\begin{pmatrix} a & 0\\ 0 & c\end{pmatrix}\mid a,c\in \mathbb{R}, a\neq 0,c\neq 0\right\}\\ K &= \left\{\begin{pmatrix} 1 & n\\ 0 & 1\end{pmatrix}\mid n\in \mathbb{Z}\right\}. \end{align*}
$G$ and $H$ have size continuum, and $K$ is countable. A coset of $H$, say $$\begin{pmatrix} d & e\\ 0 & f\end{pmatrix}H = \left\{\begin{pmatrix} ad & ec\\ 0 & fc\end{pmatrix}\mid a,c\in \mathbb{R},a\neq 0,c\neq 0\right\}$$ consists of all matrices in $G$ with a particular ratio $\frac{e}{f}$ between the top-right and bottom-right elements. Since every real number can occur as this ratio, $H$ has index continuum in $G$.
Also, the subgroup of $G$ generated by $H$ and $K$ is $G$ itself, since when $b\neq 0$, $$\begin{pmatrix} a & b\\ 0 & c\end{pmatrix} = \begin{pmatrix} 1 & 0\\ 0 & \frac{c}{b}\end{pmatrix}\begin{pmatrix} 1 & 1\\ 0 & 1\end{pmatrix}\begin{pmatrix} a & 0\\ 0 & b\end{pmatrix}.$$ So $H$ has index continuum in the subgroup generated by $K$ and $H$.