Hi Tim,

This is weird, me asking some dude on the internet for advice. As far as I know, I am a straight male with little to no attraction to men except for one instance. Four years ago I threw a party at my house. One of my friends (M) brought his gay friend (G) over, who was a really cool dude. We hit it off pretty well, and they left. M texted me the next day saying that G was interested in me and would like to talk to me.

I gave G a call, we hung out and it was amazing! We went on a walk around downtown, had dinner, watched a movie, drove around, even made out (I actually truly enjoyed it). But when it came down to "business" and he got shirtless and laid on his bed with me, I freaked out and left. However, we still talk to this day, have hung out over the years and I still feel very strong feelings about him. I really enjoy his company and I know he wants to continue what we have.

My only concern is the sexual bit. I'm really nervous because I have not done anything like that with a man and I have no idea what to expect. Otherwise I would absolutely love to have him around. Me and G live in different states now and he wants to come visit. What should I do?

C

You feel an attraction to this guy, physically and emotionally. You once enjoyed a makeout session with him but couldn’t handle anything more intimate.

If that had been the end of your letter, I’d figure you were a straight dude who had a little bi-curious episode and that was it. But you say you have strong feelings for him and want to continue what you have. That's a bit confusing as I’m not really sure what it is you guys have. A friendship? Something more?

It sounds like you might be titillated by the idea of hooking up with him, but are unsure if you really want to go through with it. Either way, that's perfectly fine and whatever you do it doesn't have to be some sort of definitive statement about your sexuality.

The only real risk here is that you might be leading G on. My advice is to be totally honest with him-- show him this letter even. He clearly seems into you, it would be unfair and, frankly, bad manners to let him think he may be getting some action on this visit, only to leave him high and dry (and sleeping on your couch) if you decide at the last minute that you can't go through with it.

If you can't bring yourself to talk with him about this beforehand, then my fallback suggestion is to meet him on neutral territory. Maybe a weekend getaway where you guys have separate hotel rooms? If things get intimate and you're comfortable with that then great, but if things become awkward then at least you both will have your own space to retreat to.

Hey Tim,

I’m in my early 40’s and mostly date men my age. In other words, I’m not running around with 20-somethings. I thought that by the time I got to my midlife years, the men around me would be in a place where they’re ready to settle down. And yet, I’m alone.

I don’t want to sound like I’m out of touch with the modern world, but I’m constantly pissed off when I go on dates, because guys are always looking at their phones. And what’s more, on several occasions I’ve caught them looking at hook-up apps! Is this our future? Are we doomed as a species to only have fleeting, ADD relationships from now until the end of time?

Over It

The bad news: while people like to poke fun at millennials for having their faces buried in their phones all day, the fact is there’s not an age limit to embracing technology, nor is there an age limit to rampant, unhinged douchebaggery.

The good news: You’re not the only one who feels this way. In fact, Thought Catalog just recently ran a whole piece about it.

We’re not doomed, but I’d be lying if I said dating hasn’t gotten more complicated with the advent of smart-phone technology. Grindr, Tinder, and all the rest have turned dating - for some people - into a process not unlike ordering take-out. Don’t like someone, you swipe them out of your mind. Like someone, see what happens. If there’s a moment where you think it’s not working out, why wait and see? Just swipe again and start all over.

So, officially and for the record: People. When you’re on a date with someone, DON’T TAKE YOUR PHONE OUT. It’s a major dick move, because it says to the person you’re with that they’re not as interesting to you as whatever is on your phone. If there’s a special circumstance, let them know, and make sure it’s damn special, like there’s a meteor hurtling toward earth and you alone know the mathematical formula that will prevent Armageddon.

Here’s the good news, OI. There are plenty of kindred spirits out there who feel the same way you do. It’s just a matter of finding them. Go to speed dating, volunteer at gay community centers, join an LGBT social club, or hell, even use an Internet dating service - which is not to be confused with a hook-up app. And make sure you are upfront about your feelings regarding smartphones on the first date. But state it positively: “I’m looking for a sweet guy who keeps his phone in his pocket when we go out,” as opposed to “Assholes who are addicted to their phones need not apply.”

Hey Tim,

A friend is hosting a party, and she said not to bring anything because she’s preparing everything and there’s even a theme, which is a surprise. But I feel weird about showing up to a place empty-handed. Should I really bring nothing, or should I at least bring a bottle of wine?

Confused Guest

If the host specifically says not to bring anything, don’t bring anything. If they say nothing, it’s always nice (but not required) to bring a little something. The rule of thumb is to always defer to the rules the host lays down.

The idea of social functions where you see your friends is that it all kind of evens out, so if your friends have parties and say don’t bring anything, the expectation is they’ll be told the same when they receive their invitation. Basically, try not to be that guy that always throws BYO parties if your friends splurge on grand meals and drinks. That’s a good way to not get invited to the next one.

More Ask O'Leary! here.

To ask Tim a question, email him at askoleary@gmail.com (and try to keep it to three paragraphs or less). Or you can be super tech-sexy and ask via Twitter.