Older Pipsqueak with his family.

I like to think Pipsqueak became a part of Luna’s guard when he’s older. Moonshine, the batpony in the upper left, was a seasoned soldier when he entered who was surprisingly friendly and affable. She was even the first among the guard to really offer friendship to him. After he worked up the bravery to ask her out, with help from the CMC, the two would begin a relationship. The results of which are their sons, Teenytiny (lower left) and Cowlick (lower right). Also, Cowlick’s wings are different colors, cuz I thought it’d be an interesting visual.

Some more info below👇

• Pipsqueak had a crush on Moonshine for quite some time, after a year of the lunar guard, but he was worried she wouldn’t see him as a possible boyfriend. She was much older and more experienced than him and he was just really coming onto his own and still feeling a bit awkward, but it was a pleasant surprise when she accepted him asking her out.
• Things were a bit awkward for Pipsqueak when he first joined since he was among the minority there; most of Luna’s night guard consists of batponies or those with batpony heritage. Moonshine was the one who helped him adjust to it and befriend the other guards, and it’s part of why he fell in love with her.
• Moonshine is the middle child among seven siblings, who are also named after various cocktails and liqours. Their mother is a mixologist who took her passion on making and serving cocktails seriously, which is why she chose that theme in naming her children
• While they did love each other very much, Pip and Moonshine never married, since Moonshine didn’t want to and Pip saw no reason to force her to do so.
• Sadly, Moonshine died not long after Cowlick was born, having contracted an infection. Moonshine’s family was utterly devastated, and her father and some of her siblings even blamed either Pip or Cowlick (or even both of them) for her death. In the present, Pip still wants his sons to have a connection with their maternal family, so he tries to encourage them to foster a relationship with them.
• Between the brothers, Teenytiny has a better relationship with their extended family on their mother’s side, mainly because none of them blame him for Moonshine’s death. It’s because of this that he tends to get caught in the middle whenever there’s family conflict, since he does want to defend his little brother but doesn’t want to alienate himself from their relatives.
• Teenytiny, like his dad, ironically grows up to be rather huge. It’s even more noticeable in his case since he grows to be Troubleshoes’ size, being taller than his father.
• Cowlick has a Trottingham accent like his father, on account of having been raised mainly by him. While he’s very small like Pipsqueak was as a child, Cowlick inherited his earth pony strength and can lift up huge objects with ease.
• Well into adulthood, Teenytiny would have yet to gain a cutiemark. Pip suspects that it might be impossible for him to have one because of Moonshine’s batpony genes (in my headcanon, batponies can’t get cutiemarks).
• Cowlick is a weak flier and struggles a bit with keeping himself in the air for more than ten minutes. Pip wishes he could help his son, and does so by encouraging him to just stay on the ground for his safety, thinking it’s the best he could do being an earth pony with a pegass son. While he does have the best intentions, it’s only made Cowlick feel worse. Luckily, he’s gotten some advice on how to deal with this from one of his godmothers, Scootaloo.
• Teenytiny is the one who got the necklace that Pip wears in the picture, having thought it would help his father to have a reminder of his mother.