Freeman, a 6-foot-6 265-pound offensive lineman from Pelion (S.C.) High, already has 19 scholarship offers with Clemson, Georgia, South Carolina, and Virginia Tech highlighting his list.
Since first contact was made, Pittman and Freeman communicate frequently.
"We text – I'd say – a couple times a week and I call him every now and then," said Freeman. "He's a great guy. He's one of the guys I don't mind talking to.
"Really, [our conversations] aren't so much based off of football and business. He wants me to get to know him as a person. He's a firm believer in every school is pretty much the same, it's just the people that are different. So just trying to get to know him – the way he is, the way he does things."
Pittman has, however, explained North Carolina's recruiting situation along the offensive line.
"I believe he said they're only going to sign two offensive linemen this year," said Freeman.
North Carolina likes Freeman as an offensive tackle. However, he's also being recruited as an offensive guard.
"It really changes – it seems like – all the time," said Freeman. "Some coaches, they think the way I move and I can pull around and lead block, they think I can play guard. But others, they think I'm athletic, tall enough, and long enough to play tackle."
Freeman plays left guard for Pelion where he was named to the All-State team for the second consecutive year last season. He also earned all-area, all-conference recognition as both an offensive and defensive lineman.
While making his May Evaluation rounds, Pittman stopped by Pelion High School last week for updated information on Freeman.
"I met with him, and he liked me and he liked the way I looked," said Freeman. "He just kept emphasizing ‘You get up here and meet our head coach and you'll have an offer and hopefully we can move on from there.'
"One of their standards is meeting the head coach. They don't offer a kid unless they've seen them in person. [Pittman] has seen me in person and he liked me, but now you've got to meet the head coach. The head coach has to see me and get to know me a little bit. It's a big investment and they don't want to mess that up. I like the way they're doing it."
Freeman hopes to squeeze an unofficial visit to UNC into his hectic summer travel schedule.
"We're trying to get all our summer plans straightened out right now," said Freeman. "Right now, if it works out we are going to go [to UNC]."
So far, Freeman has trips mapped out to Colorado, Nevada, and UNLV. He hopes to tour the schools in both Virginia and North Carolina before the end of the summer.
Freeman has already made visits to Clemson, South Carolina, Tennessee, and Wake Forest.
Heading into a summer full of campus visits, Freeman is completely open-minded.
"I really wouldn't say I have any favorites," said Freeman. "I'm still trying to keep it really wide open. After I take some visits this summer, I'll try to narrow it down for my official [visits] and we'll see what happens from then."
Freeman said he isn't exactly sure when he'll make a verbal commitment. However, he's looking for a school that will be contending for national and conference championships, has a good academic reputation, and is surrounded by quality people.
North Carolina's school colors and a few family connections have them in a good early position.
"I've always kind of been a little fan of them, because of the colors," said Freeman. "I think everybody likes that Tar Heel Blue.
"My dad grew up in North Carolina. He actually played at Wake Forest. My grandfather went to school [at UNC] after he got out of the army. And also, my mom's cousin is the dean of admissions [at UNC]."