Gifts for gang members

[Check Six]

I can't remember Lenny asking for a watch, but when I ... appropriated one, it prompted me that Lenny asked for one, so I approached him, and then button to present it to him appeared. Mary Beth asked me for a pen, and I already had one, but it won't let me give it to her, nor the candy I bought for little Jack. I still haven't found a pipe that Dutch asked me for. Did I need a "special" watch to give to Lenny? Mary Beth asked for a "fountain pen" and I think that's what I have. Jack asked for candy. Chocolate is marked as candy, and so is the candy I bought at the General Store. Why can't I give these gifts? Do I need to complete certain missions or challenges first?

[Bad 💀 Motha]

Sometimes the ability to give them the item is bugged. Sleep and try again later, or save and then reload the save. Sometimes that NPC is in middle of something, or already tasked to do something and thus the interaction to give them such item won't appear during that time.

If you are un-sure, you can check an online guide regarding this
https://www.gamepressure.com/red-dead-redemption-2/item-requests-for-the-gang-members/z4b837
to ensure you actually have the correct items in question.

[ShabDez]

Active gang item requests can be checked in the log.
You might have the wrong pen. There is the one you get from that dude that recognizes you in Valentine and then runs away. If you spare his life he will reward you with the pen. That is NOT the one Marybeth asks for.
Jack talking about choclate is only camp banter but no real fetch quest.

[Bad 💀 Motha]

And when you have given them the requested item, it will be pending in your Log unto after you actually take the reward they leave for you at your bed side table in Camp.

[Check Six]

Thanks Bad Motha.