Hi Miss Healing,

I did not quite understand the sentence about his boss, did that mean, his boss was going out on a date with the two of you? Sorry for any confusion. Also, if he really likes you, I am wondering why he didn’t just mention to his friend, that (especially his best friend) that he feels awkward that his friend would mention to him that he is into you. Be should have set boundaries, saying that he really liked you, and would appreciate if his friend not bring you up in conversations anymore. Also, if he wants to date you, and really likes you, why would he mention his boss? He does not sound very assertive, or has a clear sense of boudaries, or perhaps he is a people pleaser. It sounds like a lot of drama to me so early in the relationship, which is a red flag. I would come right out and ask him, that you feel it put you in an awkward situation about him telling you his friend liked you, and what where does he see himself with you? Does he see you as just friends? Exclusive? His behaviour is confusing and he is sending alot of mixed signals. I would test the waters slowly with this man, especially knowing you like him alot, make sure if his intentions to you. Tell him your feelings. That you prefer your dates where you two are alone together. You are setting boundaries in dating, not being needy. Now, he needs to set boundaries with his boss and friend. If he can’t do this, and keeps up with drama and mixed signals, he is not ready for a relationship. x

• This reply was modified 7 years, 1 month ago by Eliana.