Hi JT,

All through high school I had a secret crush on my best friend. Years later he came out to me, but he was still very insecure with his sexuality, and I withheld my true feelings for him. Before we left for college, I finally confessed my feelings for him, and he said that he reciprocated "some of those feelings". He even went as far as sending me that Australian marriage equality video (It's Time.), saying that it reminded him of us. 

Years passed and nothing ever progressed further than that because we only got to see each other when we were both home for breaks from school.  This last winter break we got drunk together, made out, and slept together in our underwear. Nothing more than that, but  it was one of the most amazing feelings I have ever had waking up and seeing him beside me. I've never felt more safe, loved and happy. 

We continued to hang out in the coming week or so, but never mentioned or talked about that night. When we did finally talk about what happened, he said that he regretted it and doesn't have feelings for me beyond best friends. When I asked him about all those times we talked about how we had feelings for each other, he said he was confused, he had just come out, and that he never actually had those kinds of feelings for me.

Of course I was devastated and still am. I need to get over him and moving on, but I just don't know how I can do that. He's my best friend, and I can't treat this like any other boy who broke my heart, because I don't want to lose him. Any advice?

--Unrequited Lover 

Oh, UL, my heart goes out to you. If it’s any consolation, almost everyone has faced a case of unrequited love. But I know that doesn’t make it any easier.

Here’s the thing about your BFF. He’s not the ideal guy you see him as. He pulled a major dick move when he told you he was into you. Sure, maybe he was thrown a little off-balance by his coming out process, but people know where their heart is, and my guess is he told you he reciprocated some of those feelings – and side bar, what the hell does “some of those feelings” mean? – because he was flattered by the interest and it stroked his ego.

I’m not saying he’s a bad person, but he made a bad move, and you got hurt in the process.

UL, you should put some distance between you and him. Not forever. Not even for a long time. Just for now. You need to heal a little, and you can’t do that if he’s a constant presence in your life, either real or virtual, constantly scraping open that wound.

Next, I want you to remember all the things that make you a catch. Everything that you’re proud of about yourself. Got a hobby or an interest? Work on that till you freaking rock at it. Concentrate on being the best you that you can be, because guess what, dude? It’s time to start dating.

I know it may feel a little sad and even a little futile to think about dating other people right now, but that’s what you need to do to remind yourself that love is out there for you, and you deserve it.

When you’ve done this and you feel like you’re in a good place, you can slowly start to reintroduce BFF back into your life.

The important thing right now is to get you on the right track to feeling like your own man. Mooning over someone we can’t have is something we’ve all done, and it’s exhausting. You deserve better than that.

Hey JT,

I'm 22 years old, and my boyfriend and I made it to our first year anniversary of being together! We just got engaged, I wanted to surprise him with a gift. I thought to myself, having pledged our intentions for the future in which we are married, that night when we have sex we could drop the condoms.

And therein lays my issue: unprotected sex. In my work I counsel teenagers, and that includes advocating for safe sex. I'm educated enough to make an informed adult decision that directly only affects myself and my fiancé, yet I'm crippled by the stigma attached to such a choice.

In full disclosure, I’ve had unprotected sex about 3 times in my life, all with the same man with whom I was in a 2-year relationship. We had discussed it numerous times, but I never felt like I was ready or willing to take that step. Towards the end of our relationship, though, I came around to the idea, and we did the deed sans protection. Unfortunately for me, not even two weeks later the guy confessed that he had been cheating on me throughout our entire relationship. And the reason he confessed? I needed to be tested, because he had contracted an STD. Thankfully I hadn't been infected with any diseases, but I was affected mentally and emotionally, and that all happened when I was 18.

My fiancé really is "The One" though, so I'm ready to consider unprotected sex again. And yet, I find myself still worried about being called a hypocrite because of the line of work I do. I also find myself worried about the greater impact of my decision on the gay community. Am I responsible for those younger than me? Am I turning my back on an entire generation that lost their lives?

- D

First off, D, let me congratulate you on your anniversary and your engagement.

Secondly, let me say I admire you for your work helping gay teens. It’s a noble calling and I commend you for it.

Third, I’m going to give you a gentle, loving reminder that you’re not obligated to inform everyone you know, including the teens you counsel, about the specifics of your sex life. It’s no one’s business but yours and your groom-to-be’s. So being called a hypocrite shouldn’t even be on the table.

What should be on the table, though, is what you’ve already pointed out yourself: choosing to have unprotected sex is an incredibly risky move, even with someone you love and with whom you’ve been in a year-long monogamous relationship. Adding to that very real physical risk, you’ve also been down this path before with someone you also loved and trusted, only to be betrayed and put at risk.

Here’s what I suggest.

Don’t make your wedding night this big dramatic moment where you leave the condom in the wrapper as a grandiose show of your love for each other. Don’t equate barebacking with true love, because one has absolutely nothing to do with the other. This is a mistake a lot of gay men make, and it’s understandable, but physical intimacy and emotional intimacy really are two different things.

Instead, talk to your fiancé about this. Don’t surprise him with it. If it’s something you really want to do, make the decision something you both have a say in. Get tested together, then wait a few months, then get tested again. Tell him about your experience in the past – it may be uncomfortable, but it’s a conversation you should have.

As hopefully everyone knows, the safest way to have unprotected sex is when you’re in a long-term monogamous relationship and you’ve both been recently tested. But as you yourself know, D, even then it may not actually be safe at all, because people aren’t always completely honest with their partners.

This is a decision you and your fiancé have to make together. It’s a big decision. Make sure you think it through very carefully, and you’re both on the same page. And remember, plenty of married couples use condoms, so don’t ever feel it’s something you have to do in order to prove how in love you are.

So, to recap: You’re a good dude. You’re doing good things. Your sex life is no one else’s business. Sex without a condom always carries risk. And this decision is something for you both to talk about, not for you to surprise him with.

Hey JT,

Something’s been grinding my gears for a while. I’m a young female aspiring comic with mostly gay friends, all of whom are supportive of my career. But I went out on a blind date with a guy, and he told me that he was excited to see my act, because he could tell I was really funny and he didn’t think most girl comics are funny.

What the hell? I don’t need advice on what to do with him, because I kicked him to the curb. But why do some men still think women aren’t funny, even after all the hilarious female-led comedies of the past few years?

Pissed-off Comic

Because many straight men think the world revolves around them, POC.

Seriously.

I’m not out to bash straight men. Some of my best friends are straight, I swear!

But when someone is used to the entire entertainment world catering to their specific experiences, it’s easier for them to be mystified when a different point of view is expressed. And that’s why so many straight dudes say women aren’t funny.

What they don’t understand is that they don’t find women funny because women’s experiences aren’t relatable TO THEM. But realizing that requires a self-awareness that our society, for the most part, doesn’t ask of straight men, and therefore many of them don’t have it.

It’s sort of similar to how straight men freak out when there’s male nudity in movies, seemingly oblivious to the cavalcade of boobs (boob-alcade?) that come at all of us in almost every film. To them, the slightest bit of equal nude opportunity (nude-tunity?) seems like an attack, because they’re so accustomed to having the world cater to them that they see any attempt at egalitarianism as a personal slight.

So there’s your answer, POC. The only thing I’d advise you to do is seek out the company of enlightened straight men who understand why Tina Fey and Amy Poehler hosting the Golden Globes was the best thing to have ever happened … ever.

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