We often hear how difficult dating can be. No doubt, it sure can. But it should also be fun, so I’d like to talk a little about a few common struggles I see with the goal of helping you identify them in your own dating life – and to overcome the challenges.

Number 1: Playing the “What If?” game

I go into detail on this in my previous post, but there’s a reason I’m stressing it again, and a reason why I list it first here: because it’s so prevalent. More than any other factor, this one seems to block gay men from finding and sustaining a solid relationship. So it’s important to realize when you yourself are guilty of it. If you’ve ever felt like you want to keep searching even though everything you thought you wanted is present in your boyfriend or partner, if you can’t help thinking “there’s someone better out there” or “there just isn’t a spark” then you’re playing the “What if?” game and the real question you should be asking yourself is “What am I really looking for?”

Number 2: Monogamy

This one is huge, and I touched on it a few posts ago but it deserves closer attention.

What I find with many clients is that even though most of them (70% of them, in fact) are looking for, and truly want, monogamy they feel like most other gay men are looking for an open relationship, so they feel like they have to compromise their true desires. I see a lot of “I’m willing to have an open relationship if that makes him happy, but only after 6-12 months.” They would rather have an open relationship with up-front communication than have to deal with a partner who sneaks around and cheats to get what he wants.

If an open relationship is really what you’re looking for, fine. There’s nothing wrong with that. But if it’s not, then you should realize that you don’t have to settle. If you want monogamy, then put that message out there and you will find someone who feels the same way you do.

Number 3: HIV status

This is another instance where communication and honesty about what’s true for you is key.

I encourage all of my clients to be clear from the beginning. If you’re positive – own it and share your story. Don’t be embarrassed or ashamed about it. You’ll be surprised how open and willing to listen guys will be. Because as we all know, you can be 110% safe and still get HIV. And the days of community-wide shame and embarrassment about this disease are long gone.

If you struggle with this one, support is essential. Instead of trying to contain your emotions, talk about them with a therapist or join a support network with others in the same situation. And when dating, no matter what your HIV status is, be sure about it and communicate it. If you do come up against rejection because you’re positive, try not to take it personally. It doesn’t really have to do with you – it’s the other guy’s preference for his safety. As long as both men are respectful and clear about what they’re looking for, the struggle should be much easier.

Number 4: Stereotypes/erroneous assumptions

Making assumptions is a lose-lose proposition because they short-circuit open communication and they’re almost always wrong. With my clients, these come in the form of “He just wants to sleep with me” but to give you an idea of just how off-base assumptions can be – I recently met with three men in one week who haven’t had sex in six months. So the stereotype of the gay man always on the prowl, looking for hookups, with no interest in anything more, is simply not true. (Are you listening, Patti Stanger?) The truth is, most gay men want to feel a connection. It makes sex more special, even if it doesn’t turn out to be an ongoing romance. And honestly, if it’s one-night stands and boy toys you’re after, there are much cheaper routes than a professional matchmaker that you can take to get them.

Which brings me to another situation I encounter fairly often: affluent gay men who wonder if the guy they’re dating is just in it for the money. This sometimes takes the form of the “sugar daddy” thing, where the older, affluent gay man is the provider and the younger man is “kept.” But again, I have to say that in my work I find that my clients are looking for love – the real deal – not dough.

I currently have two clients with this struggle. They are both in their upper 40s and they both love guys in their 20s. So when they communicated their assumption to me, that their 20-year-old date was just in it for their money, I replied: If you really feel that, and you’re putting yourself out there in that way [by dating someone markedly younger and less accomplished], and you’re actively inviting that into your life, than maybe that is the case. Maybe that’s why you can’t shake the feeling. But you have to own it; you have to recognize that that’s the situation you’re creating. And if the answer is No, he’s not in it for the money then you’ll know that too.

Do a see a theme in all of this? It’s about honesty with yourself and communication with others. If you can achieve these when you’re out there in the dating world, you will struggle a lot less. Now go out there and knock ‘em dead.