3 min

Gay, straight or just Craigslist (Part 1)

Doing the sexual limbo, both online and off


Is 52 y/o too old for you? Milton wrote in response to my Craigslist ad. I’m 6’2, 200lbs, run on treadmill 3x/week. I’m a nice guy looking for possible ongoing

There was something about the simplicity of his message that made him stand out amongst the others. He admitted that he was married with kids and so discretion was critical for him, which I quickly learned was common on the site. To be honest, I was apprehensive about using Craigslist personals not only because a large number of users were closeted, but also because I heard horror stories about murderers using the site to lure victims. But I was still curious about the potential to meet new people, so I decided to check it out.

I find cruising on Craigslist is a lot like fishing. You put your bait on the hook — which is a picture of my torso and cock — and you throw it into the pond of hungry fish with the intention of catching your preferred species. For me, that was an older, taller guy with big arms for no strings attached (NSA) fun. Within an hour of casting my line, my inbox was flooded with messages from hungry fish.

As I went through them, it seemed like many of the men who use Craigslist live in that space between the gay and straight world, though I wouldn’t necessarily say that they’re bisexual. The bisexual men I know are very open about their preferences and embrace the term. But these guys on Craigslist could be gay or just curious — or not yet know themselves. I was starting to see Craigslist as a cross between a haven and a purgatory for the men who are living double lives.

Some of my friends find guys like these off-putting, and for good reason. Yes, they’re dishonest, not only with their families but with themselves — and there’s something unsettling about someone who can lie like that. At the same time, I’m sympathetic because they can’t openly enjoy and embrace their sexuality.

I wrote back and said that his age was fine but asked for a body pic. He claimed that his phone was so old that it didn’t take photos, so he didn’t have any. Under normal circumstances the conversation would’ve ended there; photos are crucial to any online interaction (I later learned that the no photo shtick was generally part of the Craigslist world). So, fine, No problem, I wrote back.

Like Milton, many of the people who sent messages would just include specific physical characteristics and measurements, like I remember many did back in the ’90s. While sifting through my inbox, fellow Craigslisters told me the size of their chest and waist; the colour of their eyes and hair; whether they were cut or uncut, and so on. The phrase “drug and disease free” was also quite popular for whatever reason, and many asked if I was married.

I have to admit that after a few messages, Milton’s self-written description really stood out to me. A 6-foot-2, 200-pound man in his 50s went well with the narrative that I was after. Perhaps because I was so dissatisfied with the realities of hook-up apps like Grindr or Scruff — getting caught up in endless conversations that often led nowhere — I enjoyed this Craigslist fantasy. I decided to meet Milton for a coffee at the very least. He was elated.

I gave him my phone number and told him to give me a call — which he did that night. It came in as “No Caller ID,” so I didn’t pick up. He left a message with an explanation of who he was, fumbling nervously over his words. He said that he was calling to find out what I was into, but suddenly and abruptly stopped, an awkward silence ensuing. “I don’t know what to tell you or what to say on this voicemail,” he confessed. “Have a good day. Bye for now.”

In that message, he became a very real person to me — not a fantasy or a preference. I was initially smug after seeing the novelty in picking up the “straight” guy off  Craigslist. I now realized this wasn’t something to take lightly — the tremble of fear in his voice was a wake-up call.

He was putting his life — as he had built and lived it — on the line to find some sort of sexual connection that felt real and satisfying. Even though Milton didn’t have the strength to come out, I admired that he was making small steps to get to know himself better.

But I don’t think I felt a moral dilemma about the situation, either. And worrying about whether it was wrong to sleep with a married man seemed so bourgeois. I did have doubts about whether I would find him attractive, though. Regardless, I decided that when we met in person, I would be friendly and non-judgmental. 

The next day he called again, but this time I picked up . . .