Keeping someone awake so they stay with you is complicated, as it depends on the other person, especially if they are one of those people who don't like to go to bed late or have to get up early... In my case, I have a friend who lived with me and she had this early bird syndrome, which meant that at 7 p.m. she already wanted to be in bed so she could sleep early. She had to work early, but in my case, most of my jobs have been at night or start late, so I'm used to sleeping late. On weekends, which were our days off, I would ask her not to go to sleep so early so we could talk and I wouldn't be alone while I was sleepy. It was difficult at first to make it a routine, but we came to an agreement.
I managed to convince her by telling her that on Saturdays I would get up early to accompany her on her walks, since she really likes visiting new places and walking in mountainous areas, so we agreed that I would accompany her if on Saturday nights we went out for a drink or stayed in to watch a movie. We almost always go out, talk, and even meet up with more friends, but we only do that on Saturdays. On Sundays, we rest and also watch movies, but only until early in the evening, since she has to go to work on Mondays, and I understand that it is a difficult job, as she works more than 12 hours on her feet.
****