My 21 year old son, who is in college and still living at home, has historically been socially awkward, generally reserved and behind his peers in physical maturity (although a very handsome young man, he is around 115 pnds and 5'8"). In high school, he had a girlfriend for a brief period but she dumped him and we were never sure why. After high school, he tried to date a girl but she rejected him and a few months ago, he confessed his love for another girl who friend zoned him. He seems to have low self esteem and has commented at his frustration with girls in general and how they all seem to want tall, buff guys and only want to be his friend. As his father, I have offered advice and some life experiences to try and boost his confidence. I have tried taking him to the gym, to take up hobbies, but he always quits and just seems depressed and down. My wife and I tell him we love him frequently but something just hasnt felt right for years now.

A few years ago, he was arrested for tagging a wall. Then, a few months later, he OD'd on Mushrooms where I stayed overnight with him in the ER. Then, two weeks ago, he was arrested for a DUI where I then found that he was failing his classes in college. The DUI has now resulted in him losing his job. He is now more lost than ever and is considering joining the Army.

As I have done often before, yesterday I went to run an update on my Mac laptop that he sometimes uses for school, and he had an iMessage app/text up that I couldnt not see - a pic of himself he sent to another male that appeared to be in feminine clothing with the tag "please call me babydoll" with some sexual banter. I immediately closed the lid and put the computer back. My son has never made me think he was gay in any way up until this point (no offense intended, but sometimes you just know and with my son, it is not obvious).

I have not mentioned this to my son, but my wife and I are very concerned that his previous issues may somehow be related to repression/depression. My wife has wondered if he is exploring online relationships with men because of his frustration with girls his age, but I am thinking the opposite - that his failed relationships with girls may be because he is gay. Is it possible my wife's view could be possible?

We love our son with all of our heart and want him to feel like he can talk to us about issues like this so not sure how to proceed, if we do anything at all.