@criver no...no it isn't. It's cowardly and immature. People who are confident and have their act together face their problems head on instead of deflecting them. What you call "calculating" is actually being devious and deceitful. If she wants nothing to do with him, tell him the truth and move on, don't give him mixed signals, that's the height of rudeness. If she likes him but wants to take it slower, then straight up tell him he is moving too fast. Children lie to get what they want, being deceitful is not mature. Mature people realize that being deceitful makes you untrustworthy and they will be less likely to want to deal with you.
As for your assertion that he is desperate...tell me why it took him 5 years to approach her then and tel me why he isn't going after the two women throwing themselves at him. As for liking her tits...so what. What's wrong with being physically attracted to someone? You have no evidence that's the only reason he likes her, in fact he specifically said he is attracted to her habit of asking people questions she knows the answer to.
As for your assertion that he is desperate...tell me why it took him 5 years to approach her then and tel me why he isn't going after the two women throwing themselves at him. As for liking her tits...so what. What's wrong with being physically attracted to someone? You have no evidence that's the only reason he likes her, in fact he specifically said he is attracted to her habit of asking people questions she knows the answer to.