Dylan is very unpredictable in his thinking, which can make him a formidable ally or a dangerous opponent. The youngest of the McCloud family, he moved to RichmondValleys shortly after graduating high school to study medicine. During his time in RV, he also volunteered at a local high school, where he met and became friends with Romeo Sullivan. After a year and a half of coaching Romeo's basketball team, Dylan was forced to resign in order to keep a balanced schedule. He spent the next three years working effortlessly to obtain his Masters in Nursing.
When he finally completed the program, he decided to seek employment in Hallandale, where he could be closer to his brother. Anton was initially apprehensive about his brother's return to Hallandale, alluding to some questionable activities that Dylan got involved in when he was younger, but welcomed his brother back nonetheless. Dylan wasted no time settling in, purchasing the abandon Preston Powers Mansion and allowing Brian Fieldings and Jennifer Everestt to take a room there. His girlfriend, Garrettlyn “Garrett” Michaels, also moved in. The four bonded instantly, but strange happenings would see their friendship torn asunder.
Jennifer started receiving ghostly warnings that she would never be happy in love. Brian, however, quickly inferred that it must have been a trick summed up by Dylan. However, when the verbal warnings became physical [dead body parts], it would appear something more sinister was at work. While at Club de Moniasis, Brian then got into an altercation with a man hitting on Jennifer. That man later attacked Garrett in the Mercy Hospital ' Parking Lot. The only one who had not been victim of some peculiar circumstances was Dylan, which excited suspicion from Brian. Garrettlyn's attacker, Frankie Lancaster, who felt guilt-ridden over what he almost did, decided to confront Brian with the truth. When all the lies hit the fan, so did Brian's anger, but it was nothing compared to Garrett's. Dylan tried his best to justify his actions to his girlfriend, but it only made her more upset to realize the unfounded jealousy he had toward Christian LeBlanc.
After the revelation, Garrett ceased all communication with Dylan. Brian contemplated moving out, but Jennifer insisted that he not let Dylan drive them out. Garrett, however, couldn't get past what Dylan's jealousy had done to their relationship, and decided it would be best that she did. On behalf of Garrett, Brian made inroads with Dylan, much to Jennifer's chagrin. When Jennifer decided to give Dylan the chance to come clean about his reasons for coming after her, he tiptoed around the subject until a medical emergency took him away. After a confrontation with Garrett over the arrival of Romeo Sullivan into town, Dylan decided he needed to tell Jennifer the whole story. Unfortunately, it was too little, too late for Dylan as Jennifer slammed down his efforts and soon discovered that her ex- was in town anyway.
After months of virtually no contact, Dylan and Jennifer were able to have a civil conversation about the growing rift between her and Brian, of all things. While he didn't know for sure the reasons behind Brian and Jennifer's troubles, a recent note revealed that Brian was falling in love with her. However, instead of going to Jennifer or Brian with it, he decided to lord it over Romeo's head. Romeo tried his best to appear unfazed, but when Dylan sniffed out that Romeo was worried about Brian's growing feelings for Jennifer, he realized the note could spell the end for Jennifer and Romeo.
