Between 7-9-ish, I would say? Maybe a bit earlier on weeknights? Boston's a pretty early city for both dining and nightlife; many restaurant kitchens close by 10 or 11.
Word to the wise, Neptune doesn't take reservations, so it's best to try to go there at off-peak times. It's my favorite "playing hookey from work and having a late lunch" restaurant.
I would also like to add, having been several times to Montreal, that the Boston dining scene tends to be a rather noisy affair, so be prepared. There are restaurants that offer a very quiet, relaxed atmosphere, but most places it's more festive and you may find yourselves needing to talk quite loudly to hear each other.
About 8 PM is prime reservation time.
Most, not all, good restaurants serve dinner until around 10pm during the week, 11pm on weekends.
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