A creepy guy stalks the same woman for thirty minutes every day for three days in a row.
A creepy guy stalks a woman for ninety minutes continuously on a single day.
Which scenario – if any – constitutes criminal harassment? Section 264(1) of the Criminal Code describes a range of harassing behaviour:
264 (1) No person shall, without lawful authority and knowing that another person is harassed or recklessly as to whether the other person is harassed, engage in conduct referred to in subsection (2) that causes that other person reasonably, in all the circumstances, to fear for their safety or the safety of anyone known to them.
(2) The conduct mentioned in subsection (1) consists of
(a) repeatedly following from place to place the other person or anyone known to them;
(b) repeatedly communicating with, either directly or indirectly, the other person or anyone known to them;
(c) besetting or watching the dwelling-house, or place where the other person, or anyone known to them, resides, works, carries on business or happens to be; or
(d) engaging in threatening conduct directed at the other person or any member of their family.
So what does the word “repeatedly” mean in the context of criminal harassment? Does it mean at least twice? Three times? Well, in R. v. Venn, 2014 ABPC 284, the Court expressed a more nuanced view:
 The Ontario Court of Justice (General Division) in R. v. Belcher (1998 CarswellOnt 192), 50 O.T.C. 189, considered the nature of the ‘following’ that is required to found the charge under the subsection in question. At paragraph 20 the court summarized the authorities stating that the repeated ‘following’ contemplated by the section describes conduct that occurs more than once.
 However, the ‘following’ need not occur over and over again separated by any particular amount of time. Rather, the meaning in the criminal law context means “persistently” following. The court stated that focussing on persistent following “which demonstrates resolve to do so”, would help avoid criminalizing innocuously following another person even if annoying or prolonged.
In R. v. Ohenhen, 2005 CanLII 34564 (ON CA), the Court of Appeal for Ontario found that sending two letters over the span of 18 months constituted “repeatedly communicating”. In examining past case law, the Court rejected suggestions that “repeatedly” meant three or more:
 I do not interpret these reasons to say anything other than that in the circumstances of that case the three incidents which were the subject of the charge were sufficient to meet the charge of “repeatedly communicating”. The statement that “three communications would seem to be the minimum number sufficient to justify being described as ‘repeatedly'” was nothing more than a Crown submission and was not specifically adopted by the court.
The Court went on to examine Belcher and other cases in a detailed manner, and ultimately reached this conclusion:
 In my view, the dictionary definitions of the words “repeat” and “repeated”, from which the adverbial form “repeatedly” is derived, lead me to conclude that conduct which occurs more than once can, depending on the circumstances of the case, constitute “repeated” conduct or conduct which is “repeatedly” done and the section is met. In my view, it is unnecessary that there be a minimum of three events or communications. “Repeatedly” obviously means more than once but not necessarily more than twice.
 While one instance of unwanted conduct can be sufficient to satisfy s. 264(2)(c) and (d), it will not be sufficient to satisfy s. 264(2)(b). More than one instance of unwanted conduct will be necessary to meet paragraph (b); however, in my view, there is not and should not be any minimum number of instances of unwanted conduct beyond this to trigger these subsections. Provided the conduct occurs more than once, in my view, the actus reus can be made out. It will be a question of fact for the trier in each case whether there has been repeated conduct. The approach is a contextual one. The trier will consider the conduct that is the subject of the charge against the background of the relationship and/or history between the complainant and accused. It is in this context that a determination will be made as to whether there has been repeated communication. On the facts of this case, it was clear that neither of the communications could be characterized as i nnocuous or accidental. In the context in which they were made, these two communications would be [page581] sufficient to constitute “repeatedly” communicating as set out in s. 264(2) (b). In my view, it was entirely appropriate for the trial judge to use the standard charge language on this point.
 Although not in issue on the facts of this case, trial judges should be cautious in using the standard charge language in all cases. It seems to me that defining “repeatedly” as being more than one communication is not always appropriate. In some cases, the jury will have to consider the context in which the communications were made, the intent of the accused and possibly other factors to determine whether the communications were repeatedly made or were innocuous or accidental. Perhaps a more appropriate instruction would be to advise the jury that communication that occurs more than once can constitute repeated communications depending on the context and circumstances in which they were made.
The Court of Appeal for Ontario upheld the conviction for criminal harassment and found the sentence to be appropriate:
 Lastly, the appellant requests leave to appeal his sentence and if leave is granted, appeals on the basis that in all the circumstances, his sentence is overly harsh. Counsel advised the court that he has served his sentence.
 The appellant was sentenced, in effect, to three years’ imprisonment. After being given credit for the time he spent in pre-trial custody, he was required to serve a further 18 months. The sentence was to be followed by two years’ probation. The appellant has an extensive record dating back to 1990; it includes weapons offences, aggravated assault, assault with a weapon and at least four convictions for uttering threats. In my view, the sentence was manifestly fit in all the circumstances and I would not interfere with it. In view of the fact, however, that the sentence has been served, I would deny leave to appeal sentence.
My takeaway from all of this? There is no magic number of incidents required for criminal harassment to have occurred. Victims do not have to be followed for a minimum of three separate times. Nor do there have to be a minimum of three separate communications.