The Massachusetts statute is structured differently and doesn’t really seem comparable. The Florida statute says “repeatedly […] harasses”, but “harass” is defined in the singular as a course of conduct. You need at least two incidents of harassment, and each incident of harassment is its own course of conduct.
Put another way you need at least two incidents of at least two “acts” each. For statutes in other states it probably makes sense to consider an extended incident a single “act” for the purposes of a course of conduct. I think even repeat violence statutes in Florida consider it a continuous act if there isn’t a time gap. But in Florida’s stalking statute, “course of conduct” is defined as “a pattern of conduct composed of a series of acts over a period of time, however short, which evidences a continuity of purpose.” The defendant must have repeatedly engaged in courses of conduct directed at a specific person which caused significant emotional distress for no legitimate purpose.
Cash v. Gagnon, 306 So. 3d 106 (2020) reads “A course of conduct requires multiple acts that are separated by time or distance” but I’m fairly confident that was written by mistake, as the repeated “acts” of violence in the cited case are analogous to repeated harassment in a stalking case.
If I haven’t bored you to death already, here is how I would interpret the Florida stalking statute in a traditional case, and then below is an analogous VR case.
Warning: depictions of sexual harassment and virtual sexual assault
Traditional example
Monday: Alice is watering her plants by the sidewalk in front of her house. Bob, an unfamiliar neighbor, is walking down the sidewalk in an unkempt state. Bob turns toward her and lets loose a wolf whistle. Alice tells him to piss off.
Wednesday: Alice is watering her plants by the sidewalk in front of her house. Bob sneaks up behind her while she’s bent over and says “I like the view,” at which point Alice throws a pot at him and bolts inside, shrieking. No physical contact is made.
I say these would constitute stalking under the Florida statute.
The first instance of harassment is on Monday. The acts of looking at Alice (1) and wolf whistling (2) constitute “a series of acts over a period of time, however short, which evidences a continuity of purpose.” In context, this pattern of conduct doesn’t serve a legitimate purpose and a reasonable person would expect it to cause substantial emotional distress.
The second instance of harassment is on Wednesday. The acts of sneaking up behind Alice (1) and saying “I like the view” (2) constitute “a series of acts over a period of time, however short, which evidences a continuity of purpose.” In context, this pattern of conduct doesn’t serve a legitimate purpose and a reasonable person would expect it to cause substantial emotional distress.
Two instances of harassment count as “repeated” harassment, so I say taken together the two incidences above would qualify as criminal stalking (if the prosecution can convince the jury of malicious intent.)
 
VR example
Now for a more relevant example, if the OP were to have his character sue under Florida law as interpreted by me (non-lawyer).
Friday: Cassie is sitting in her room. Dave, a friend of a friend, DMs her unsolicited to ask if she’s “dtf” (down to fuck). Cassie responds “gross stop I don’t know u”, Dave responds “yet”. Cassie blocks him on Instagram.
Saturday: Cassie is sitting in her room with her BrainVR set on. In the virtual environment, she is in a friend’s private room, waiting for her friend to return. Dave is in his own house with his own BrainVR set on. Dave and Cassie share the mutual friend, and Dave’s avatar enters the same private room in the virtual environment. Dave sees Cassie’s avatar and commands his own avatar to grope hers. Cassie doesn’t resist, paralyzed by fear and horror like a deer in headlights. Sensory feedback is relayed directly to both of their brains as his avatar gropes her avatar’s breasts, then buttocks. Maybe two minutes pass before the friend returns and Dave disconnects from the service.
I say these also constitute stalking under the Florida statute.
The first instance of harassment is on Friday. The acts of sending two unsolicited DMs to elicit sex (1 & 2) constitute “a series of acts over a period of time, however short, which evidences a continuity of purpose.” In context, this pattern of conduct doesn’t serve a legitimate purpose and a reasonable person would expect it to cause substantial emotional distress.
The second instance of harassment is on Saturday. The acts of sending commands to have his avatar grope Alice’s avatar’s breasts (1) and then buttocks (2) constitute “a series of acts over a period of time, however short, which evidences a continuity of purpose.” In context, this pattern of conduct doesn’t serve a legitimate purpose and a reasonable person would expect it to cause substantial emotional distress.
Two instances of harassment count as “repeated” harassment, so I say taken together the two incidences above would qualify as criminal stalking (if the prosecution can convince the jury of malicious intent.)
 
~Max