I have given you my line of thinking offline, since you haven't posted your 'dilemma'. However, if you think you can handle the consequences, then by all means, put on an Oscar-winning performance of "OH, wow what a coincidence" and watch him squirm, feel uncomfortable, which will hit at least one or two of his hidden fear buttons, and possibly lead him to anger, and feeling 'followed' and wondering just how this 'coincidence' happened, etc.... If you're ready to watch him squirm and possibly get angry and possibly retreat into his cave licking his "i got caught" wounds, then by all means, Dear, go!
BTW, are you really that good an actress? I know that my eyes, and the flush of anger in my face, would surely give me away . . . BUT, you're not me. . .