On his daughters' wedding day; Jon thinks back over their family life and regrets the decisions he'd made, until he is reassured that they always knew he was there.
Trip and Jon spent Saturday together with their children, talking about what might have happened, and how things could be different. Leading to one making a big decision. (Jon/Erika and Trip/Hoshi)
After Jon's first year as an ambassador on Andoria, he realises how much of his families life he is missing, and tries to convince his wife to bring their family to Andoria with him. Set in 2169.
After the events of "Observer Effect", Jon realises it's time he makes his decisions about his personal life clearer, the first of them being telling the love of his life that he still wanted to be with her, and that he was an idiot for letting her go the first time.
Jon wakes up to discover Serena has built a fort, and named it Columbia. Erika picks a great time to tell Jon some big news.
Jon is called to a Starfleet celebration, and needs to be reminded that there is always someone beside him, even when he's alone.