Testing the waters with a crabby male. How would I know when to move forward, I doubt he will...

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crabluvrgurl
@crabluvrgurl
10 Years

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I have been seeing a wonderful crabby male for about 3 months and we've been getting to know each other and taking things very slowly. We have not kissed and have not been physical.
From the beginning, I have suspected that he has been hurt badly as he has no friends that dominate his time or come by his house. Other than going to work and going to the grocery store he is ALWAYS home. I've gathered from comments he's made about his mother that they have a strained relationship. Him and I speak daily and spend a few evenings a week together (unless he decides to go into his shell and I've been secure enough to let him go into his shell as we have had no interactions that would have driven him to the shell.
He always comes back and is his normal self and it's never been over 1 or 2 days tops.

Well..... Sunday afternoon he unexpectedly opened up about the relationship with his mom (in the past he has said he didn't want to talk about it) and her "useless boyfriend" You can tell it bothers him that the boyfriend is a moocher living off of his mother. Also last night after dinner at his house he offered $ 20.00 to give him a foot massage, I replied, I do not need your money. I will just give you a foot massage, He was thrilled So he retrieves his massage lotion and I proceed to give him a thorough foot massage and then he asks; can I massage his shoulders? Which I told him no problem. The truth is I enjoy our time together and after the massage and watching some Monday night football, I left and went home. I feel these have been break thrus in opening up to me and I want to know how I should proceed? Wait for him or if he asks for a massage tonight should I go in for the kiss? Please the advice would be appreciated.