Gay Self-Hatred

I am gay and have a gay friend who is constantly making negative remarks about other gay people and homosexuality in general.  I have confronted him on this on more than one occasion, but he seems unable to talk about why he feels the way he does. He is Catholic, and may have absorbed some of their virulently homophobic attitudes. I think he has many good qualities, I like him, but his homophobia and negativity often make it difficult to deal with him. We are both in our mid-forties. He has no partner, but I can't imagine he will ever get one with his current attitude. Is there any way to help him get over his internalized homophobia?

Homosexual men like this have hated themselves for so many years that it's often difficult if not impossible to get through to them. That doesn't mean there isn't a chance, but your friend has to admit that there is a problem. He is gay, he can't change it, yet he hates himself and hates being gay, and it is all so unnecessary. You are undoubtedly right that his Catholic upbringing has done a number on him, as it has on so many other gay men and lesbians.

Often the self-hate of people like this is commingled with other negative feelings they have about themselves regarding their looks, weight, frustrated ambitions, loneliness, and so on. Your friend probably has a whole long list of grievances. His negative feelings about himself [aside from his homosexuality] feed off his negative feelings about being gay, and create a vicious circle that he's trapped inside.

Men like this are often expressing negative feelings because they feel rejected by other gay men. He has no boyfriend, probably does not go out on dates, and let's not even get into his sex life. This feeling of being rejected leads to him hating being gay and blaming his homosexuality on all of his problems -- he would be happy, he feels, if only he were straight. Sadly, it doesn't work that way. [And there are plenty of miserable, lonely heterosexuals out there for which being straight is not a magic cure-all.]

Sit down with him and tell him how utterly oppressive you find his attitude to be. In a tactful way help him to maximize his assets and minimize his less attractive features. He can't change his orientation so he might as well accept it, embrace it, and develop some pride in himself. Suggest he get some counseling and that a gay or gay-friendly therapist could help him feel better about himself. And it wouldn't hurt to remind him that more and more people are finding the Catholic church and other religions negative attitudes toward homosexuality to be outrageous and totally out of date.

I mean, guys like this are deep down miserable and they don't need to be.

If he doesn't listen to you, refuses to even talk about it, and his behavior and remarks continue to bother you, then you may just have to lose him as a friend.

Transgender Friend?

Dear Bill:

A strange question: I have a friend whom I've known for about four years. He is a man, but I have a fairly strong idea that he might be transgender. He's a great person and I value the friendship very much, so I don't want to rock the boat, but he has never brought up the subject that he hasn't always been a man.

I wouldn't say it's vital for me to know for sure...I would definitely want him as a friend, regardless. I'm gay but romantic considerations aren't really a factor here...he has a girlfriend and is thinking of marriage. It's just that I'm curious, it seems to be limiting the conversation -- there is an invisible elephant in the room that neither of us is talking about.

Should I just wait for him to bring it up? Clearly, I can't just say, "You're transgender, aren't you?" It would be amazingly awkward, even more so if I'm wrong.

It's understandable that you're curious about this situation but you're right that it would be awkward -- and worse if he's not transgender. If he is a Trans Man he may be thinking or hoping that he completely "passes" so you'd also risk shattering his illusions or confidence. I would wait until he brings it up, which he may eventually do as you grow closer as friends. Does he know that you're gay? If not, coming out would be a start -- you're both members of the LGBT community even if he isn't gay apparently. Have you met the woman he's going to marry? She may turn out to be transgender as well, which would be another sign. Not that all transgender people pair up with other Trans Men or Women, but it does happen, especially if they want a partner who will understand them and be non-judgmental.

Just hope that some day he'll take you into his confidence.

The Guy That Got Away

Dr. Bill, I'm a man in my late forties and about a year ago I dated a man who was somewhat younger than me -- all right, a lot younger than me -- and he seemed to really be into me. Because of the age difference and because he was so attractive, I hung back a little and sort of let him do the pursuing. I guess I couldn't quite believe that he was really that interested in me or I was just afraid I would be seen as the desperate older man stalking the younger guy or something like that. In any case, I took my time responding to texts and phone messages and eventually I stopped hearing from him. I always hoped that we would run into each other again, but I checked out his facebook page and now he has a lover -- closer to his own age, of course. I'm happy for him , of course, but I'm left with the feeling that had I only not hung back, pursued him more ardently, I might be his lover today. I'm not even certain what I'm asking. I haven't checked out his facebook page since and I won't but I find myself thinking about him a lot. I wouldn't quite call what I feel heartache, but nonetheless it hurts. What do you think and what can I do to make this feeling of regret and loneliness go away? I don't think anyone like him will ever come my way again.

Get out of the house, join gay dating sites if you haven't already and follow up on interested parties, hit a bar that caters to men your age or mixed ages, call up some friends, have drinks or dinner and exchange war stories, commiserating over romantic misfires. Stay away from friends in happy relationships for awhile as they may only remind you of what you're missing. Have some hot consolation sex. Or hot chocolate if the former isn't available.

I have been in a similar situation, and you'll never know if the guy stopped calling you because you didn't pursue him enough, or because he just wasn't that into you when all is said and done, or if he, frankly, ultimately wanted a man in his own age group. You may never know, so forget it. Stay off his Facebook page -- you don't need to see photos of him and his lover enjoying happy domesticity. Or getting married! Believe me, you really don't need that torture.

You say that you don't think anyone like him will ever come your way again. First, you can't really know that for certain. Second, the next man you fall for [and who will hopefully fall for you] may not be as young and handsome as this guy, but he will still be "Mr. Right" if it turns out he's The Guy. You're certainly not too old to find a long-lasting relationship. [I mean I know men in their seventies who have fuck-buddies, sometimes much younger, or who have found soul-mates in their senior years -- you never know!]

Do not think of this guy as your last chance. There's always somebody interesting around the corner, you just gotta get out there and meet him. Take it from one who's been there: after awhile you won't even remember what this guy looked like [admittedly it might take a little longer than with other guys].

Good luck!