Making friends will always be perhaps one of the hardest tasks anyone sets off to do. No matter how young or old someone is, making friends never gets any easier. Everyone has likes and dislikes; which sooner or later causes heads to butt over who has to change their likes or dislikes to better suit the group. When that happens, friendship between those few is ruined. So, most are afraid to make that first contact with someone. It's common nature to fear rejection or the possibility that down the road things won't work out. That's one root reason why making friends is never easy...
However... Those people have the wrong idea entirely. You shouldn't take the time to find friends for yourself. No. You don't know anything about yourself. Who're you to say what's best for you? If you pick your friends, you'll just end up with bad seeds or fair-weather friends. It's up to your dearest and most trusted companion to sort through every possibility to find who is or isn't right to be your friend. That's why Pipsqueak is lucky to have such a dedicated friend like Princess Luna.
"Luna, I admire your well meaning intentions..." Celestia leaned down to whisper into her sister's ear while also looking at the extensive line of assorted fillies, colts, mares, and stallions stretching for nearly a mile before Luna behind a desk, "...But this all seems unorthodox."
Princess Luna, her horn's magic gripping around a collective of papers tapped the bundle against the face of her desk, looking as professional as she saw this job to be. "Unorthodox measures are required for unorthodox circumstances, sister." Luna looked over the long line of ponies that responded to her 'want ad' listing Pipsqueak as 'needing a friend'. "My dearest comrade is in grievous neglect of a multitude of friends to 'play' and 'jostle about' with. And I shall be to Tartarus if I did not lend my aid in finding him friends!"
Once more Celestia looked over at the long line of waiting ponies and shook her head. As stressful as the sight was, Celestia still smiled and took her leave down the halls of the castle. "Do as you wish, Luna. Just please don't destroy the castle..."
Left to herself and the willing applicants out before her, Luna looked down to the start of her list of possible friends for Pipsqueak. It was a long list with many hopeful appliers, but only the cream of the crop could be picked to be Pipsqueak's best friends. Luna was more determined for this task then any other she had faced before. With pride welling inside her for the at hand, she spoke the first name...
"Now... Gilda, correct? If your transcript is to be believed, you are a practical-joker enthusiast?"
"Um... Yeah? I like playing tricks on people, if that's what it means."
"Hm, indeed. That is well and good... But what should happen if Pipsqueak broke his leg tripping over one of your 'tricks'?"
"Um... I guess laugh?"
"You papers check out very well. Dedicated, hard working, and you work very well under pressuring situations. Overall, you seem like an ideal friend, Little Strongheart."
"I am most pleased to hear that."
"Nevertheless, if we were to put all of that aside... Tell me how you would handle a case where buffalo were to trample Pipsqueak."
"I would veer the stampede away from him and have them trample over anywhere else."
"Fair answer. Yet, your immediate response should always be 'push Pipsqueak out of the way and have yourself trampled'."
"But... What would it matter if I safely prevented anyone from being hurt?"
"The safety of everyone else pales in comparison to your friend. Even more-so when that friend is Pip."
"...Discord, what are you doing in this line?"
"I thought it was the line for the bathroom."
"There exists a multitude of bathrooms outside of the castle! Why not use one of those?"
"Oh! Hogging all of the good TP for yourself, huh? This is a dictatorship!"
"You talk a big game, you spout a plethora of recommendations, and you have a redeeming list of accomplishments. So, I must inquire... Why, Pound Cake? Why?"
"...Bah! Mmmm Pie! Heh-heh-heh! Up!"
"Mhm... Your argument is compelling, I yield to that... We shall be in touch."
"...It says here you have been fired once?"
"I... I quit."
"Regardless, that does not look too favorably on you."
"I know... But I had to."
"Such is what all deserters say. Moving on... Your previous employer wrote that you were a 'blind-eyed-wannabee'? How would that benefit Pipsqueak?"
"It wouldn't... But I have a lot of other things I can offer. I'm really great with kids, actually."
"You do understand this isn't a babysitting job, correct?"
"Yes, I know. Really, I don't have many friends my own age... So, I thought I'd start--well--small."
"Hm... You have a certain modesty about you... Very well. Let me ask you this: what would you do if Pipsqueak broke his leg?"
"Splint it back up on the spot with a medical kit."
"What if he was about to be trampled?"
"Throw myself in the way."
"Under attack by a hydra?"
"Cover myself in honey and have it attack me."
"What if Pip fell down a well!?"
"Break down the well and be sued by the town for breaking it to save him."
"...When can you start, Coco?"