(1) See the Rosh 1:2 who writes that Shmuel is even discussing a case where the Chasan and Kalah were talking about matters of Kidushin - Asukin b'Oso Inyan. Hareini Ishech is actually worse than saying nothing. The Korban Nesanel (letter Pei) explains that since he added the words Hareini Ishech he actually made things worse with this addition, because it means that he retracted from his original intentions. Since they were speaking about getting married it would have been sufficient to give her money without saying a word because we can assume that the fact that he gave her money must mean that he gave it in order to make a Kidushin. However since he said a phrase which is inappropriate to Kidushin - Hareini Ishech - this must mean that he decided he did not want Kidushin after all. The Torah (Devarim 24:1) states "When he takes a woman" i.e. he has to take her and not that he should take himself to be for her, so Hareini Ishech has no connection with Kidushin and the fact that he used it suggests that he is trying to steer clear of Kidushin.

(2) There is an opinion that disagrees with the Rosh. Rabeinu Yerucham cited in the Beis Yosef EH 27:6 writes that some say that it is certainly Mekudeshes if he said Hareini Ishech when they were Asukin b'Oso Inyan and others say that this is a doubtful Kidushin. The Darkei Moshe (6*) explains that since he had previously spoken to her about Kidushin this overrides the faulty formula of Hareini Ishech. In other words, there is a contradiction between the Chasan's acts and between his words. His words suggest he does not want Kidushin but the fact that he gave her money just at the time they were talking about Kidushin suggests he does want Kidushin. According to Rabeinu Yerucham, in this particular case we say that his actions cancel out his words - either we are certain that they cancel out his words or at least we have a doubt that they might cancel out his words.

(3) However the Pischei Teshuvah EH 27:20 writes that according to Rabeinu Yerucham who is stringent on the words Hareini Ishech, this is only if he was speaking previously about Kidushin. Then we say that Hareini Ishech is equivalent to keeping quiet and saying nothing. It follows that if they were not Asukin b'Oso Inyan, and he said Hareini Ishech, it is as if he said nothing so there is no reason why we should be worried that the money he gave her was for Kidushin.

[What the Pischei Teshuvos writes that Hareini Ishech is equivalent to keeping quiet may not be the same as what I wrote above (2) because I suggested that Hareini Ishech indicates that he does not want Kidushin but Asukin b'Oso Inyan suggests even more strongly that he does want Kidushin, whereas the Pischei Teshuvos appears to hold that according to Rabeinu Yerucham, Hareini Ishech is entirely neutral.]

(4) In summary, according to the Rosh, Hareini Ishech is worse than saying nothing and suggests that he does not want Kidushin, whereas according to Rabeinu Yerucham it is equivalent to saying nothing, so without Asukin b'Oso Inyan, there is nothing to suggest he wants Kidushin.

D. Bloom