What time does he eat dinner? I feed my daughter (15 months) right on 5pm. She has milk at 6pm. Then we have a little play and stories until 6.30pm and she's out. She wakes up during the night and doesn't really self-settle but will go straight back down with a quick cuddle.

Could it be new teeth coming through. BD was really clingy and restless each time she was getting a tooth.

My only suggestion is to feed him earlier.