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At five, taking something that doesn’t belong to him doesn’t mean this is becoming part of his character. Kids this age usually understand that things belong to other people and that they shouldn’t take them, but their impulse control and ability to think through what happens next are still developing. He may see something he really wants, act in the moment, and only fully feel the weight of that choice once it’s discovered.

The crying and “I don’t remember” are worth noticing too. He may be trying to avoid a difficult conversation, but he may also feel overwhelmed, embarrassed, or worried about disappointing you. When kids are flooded with emotion, it can be hard for them to explain what happened clearly. A few things to try:

• Separate the behavior from who he is. Avoid calling him a thief or asking, “Why would you steal that?” Instead, say, “You took something that wasn’t yours, so we need to bring it back.” You can correct the behavior without making him feel like it defines him.

• Make returning it about repair, not punishment. Go with him to give it back if you can. Keep it simple: "This belongs to your friend. Let's give it back together." A calm, matter-of-fact return teaches the lesson far better than a lecture does.

• Skip the interrogation. Asking "did you take this" over and over when you already know the answer just backs him into a corner where lying feels safer than telling the truth. Try, "I found this in your bag. It's not ours. Let's figure out how to fix it," instead.

• Talk about wanting, out loud, before it happens. "I really wanted that toy at the store today. It was hard to leave without it." This gives him language for the feeling itself, which is often what is missing at this age.

• Praise honesty specifically when you see it. "You told me the truth even though it was hard. That matters to me." This builds the muscle you actually want for the moments that count.

You can consider adding a check-in if it keeps happening. If he’s bringing things home regularly, briefly check his backpack or pockets together before leaving school or a friend’s house. Try to keep it neutral: “Let’s make sure everything coming home belongs to us.” This doesn’t need to become a permanent routine. It’s a temporary support while he works on slowing down and remembering to leave other people’s belongings behind.

As for whether this is something to worry about long-term, taking things without permission can happen at this age and often improves as impulse control and empathy develop. It’s worth looking more closely if it happens frequently, involves planning or repeated hiding, continues despite calm and consistent correction, or comes alongside other significant behavior changes. In that case, or if your concern continues, bring it up with his pediatrician.

It sounds like rocking him to sleep has been such a sweet part of this stage, so it makes sense that changing it feels a little sad. But it’s also okay to admit that the routine isn’t working as well anymore. At seven months, many babies can begin learning to fall asleep in the crib without being rocked all the way to sleep.

The crying piece is part of this too. Some protest during a change like this is expected, but how much crying you’re comfortable with is personal. Some parents prefer a slow, gradual approach with more support. Others do better with a clearer, more structured plan. The best approach is one you can follow consistently without feeling like you’re pushing past your own limits.

Here are a few approaches to try:

• Put him down calm and drowsy, but still awake. Rock him until he’s relaxed, then place him in the crib before he falls asleep. If that feels like too big of a jump, gradually shorten the rocking over several nights.

• Pause briefly before stepping in. If he fusses, give him a moment and see whether your voice or a hand on his chest helps. If the crying escalates or something feels off, respond and help him calm.

• Keep the routine predictable. Read a book, rock, dim lights, a song, then the crib can help him start connecting those steps with sleep.

• Expect some protest. You can comfort him in the crib, use brief check-ins, or pick him up to calm him before trying again. Choose an approach that feels manageable and stick with it.

• Look for progress over several nights. One hard night doesn’t mean it isn’t working. Consistency still leaves room to offer more support when he’s hungry, sick, teething, or having an unusually difficult night.

If you want to go deeper on any of this, my PedsDocTalk Sleep Guide has everything in one spot: the research on different sleep training approaches, troubleshooting for regressions, and courses if you want more structured support. It's worth a look if you want to feel more confident in whatever you decide here.

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