Have to say the Hailey route broke my immersion a bit. The other LI progressions felt quite organic according to their individual personalities combined with the MC choices of where his head was currently at/what he was currently comfortable with - the option of turning down Sarah the first time as an example.
Hailey just felt...rushed? Fine as far as other VNs typically treat this kind of thing, but it felt out of place in TMP largely because of how realistically everything else is portrayed. But in this case you have not only the MC's baggage but a large amount on Hailey's end as well; the kind you can't just flip a switch or make a choice to get over. Plus the enormous age gap and maturity disparity - Hailey is extremely mature in some aspects, but is certainly portrayed as having a giggly little girl side in a number of scenes as well.
The baggage of both combined with the age disparity made the "long evening" feel out of place to me as extremely rushed and frankly exploitative. A lot more communication to work out those issues together, followed by a slow burn progression to build trust feels like the only realistic path for someone like Hailey. Might be alone in thinking that, but my 2 cents.