Ask a Pro: Quickie Edition

Dear Head Pro,

So I dated my first boyfriend for about two years in high school before we ended things because of going to different colleges (I ended up staying in the city and he went to an upstate school).We still saw each other pretty often when he came back for holidays and such, but we didn't exactly do the long distance thing. Eventually, things just came to an end. To be honest, I always had a crush on his attractive SAB best friend. Skip forward about another year, and there were a few occasions where I slept with said SAB. Obviously neither of us really wants this getting back to my ex, and afterwards he’d talk about how it was somehow hotter because it was a secret.

Here’s my question: Do guys usually feel bad about sleeping with their best friend’s ex? Or is it something that varies from bro to bro depending on their level of shadiness?

Chicks before Dicks?

Yeah, guys do, and yes it depends on shadiness. That’s kind of self-evident in the fact that he doesn’t want your ex finding out either. Most guys avoid it, but there is something of a statute of limitations involved. Some girl my friend went on a few dates with a couple of years ago becomes fair game pretty quickly. An ex-wife would probably never be ok. In general, you stay away from your friends “milestone” relationships – first serious girlfriend, first lay, first anal 3-way, etc. It’s not an issue of “ownership” or any bullshit like that. It’s just that most guys have enough courtesy to know that treading on that kind of ground could dredge up too many unpleasant memories.

Dear Head-pro

[Long paragraph of useless bullshit, summary is that this couple is on date number five and have been taking it slow]

To get to the point, he ends up going down on me last night which I was in no way expecting…I wasn't planning on doing that at all, but it only seemed right to return the favor. So I did, he finished, on himself, because I didn't feel thaaat comfortable, and now I'm wondering what if any of these were the right move. 1.) Was it way too intimate for me to go down before we ever had sex? After all I was just following his lead… 2.) Does it look super prudish that I didn't spit OR swallow? Should I have just let him……since I was already deep throating where he pees? I'm just afraid he's going to decide I'm kind of wack or that I have some kind of aversion to semen or somehow I'm just weird as shit…really like this guy. Any thoughts welcome, including the kind where you berate me for being weird as shit.

Normal I Swear

Nothing like getting AMBUSHED BY CUNNILINGUS. You kind of touched on my feelings on it, which is that since you’re already up in my business there’s no harm in letting things conclude in there. Then again, it’s your mouth and I imagine an ejaculating penis probably feels like you chomped down on a squishy bug or something. In general, I think most guys are just happy to have the blowjob and aren’t too worried about how things end up. Hell, for three years running now the Zagat Guide has listed the vagina as “the best place to store a penis at any given time,” and sometimes guys still like to pull out and blast it on your funbags. He’s not gonna pull out his moleskine and write “Decent b-jibber, forced external climax. Do not call again.”

Dear Head Pro,

Let me start by saying you're fucking amazing and your answers to some of these questions have me convinced I'd probably want to marry you, so here's my dilemma: I am really annoyed right now by this guy I went out with and need some pro-spective. I met him at a party briefly and then got a call the next day (yes over the phone) saying that when he saw me he thought I was so gorgeous that he had his friend give him my number. He asked me out and we ended up having an amazing first date – he was a gentleman, we have a ton in common and a lot of chemistry. He gave me compliments all night and when we talked about what we look for in another person he pretty much listed all the qualities he had complimented me on earlier and when I came back from the restroom he told me the waiter gave him my seal of approval. It is now 3 days later and nothing – no text, no call, no contact. With every date I've been on in the last year I haven't had one where the guy hadn't texted me at the end of the night saying he had a good time and those dates weren't half as good as this. My question is am I crazy for being upset about not hearing from him after 3 days? Do you think he's just playing games or do you think something else is going on?

Slightly trippin

No, I don’t think you’re crazy, but three days is still only three days. Even if he’s really over the moon for you he might have other shit going on. Or lost his phone. Or had an ex come back into his life. Or he died. Or maybe he’s mad you didn’t throw yourself on his dick after such a sappy, cliche date. In general: Guys rarely apply the “wait three days to call” rule you see on TV and in movies, and this is the reason. You try it maybe once before you realize that it’s juuuuust long enough for girls to go from intrigued to annoyed. Plus, it’s bad form to pull it after a first date. Always save that shit for later on when she’s had a chance to invest in you emotionally.

Dear Head Pro,
So I have been hooking up with this guy for five months. Five long months consisting of mostly drunk sex. With all those drunk hookups, however, there have also been some drunk conversations about having sex with just each other. The key word there being that they were drunk conversations, so I am assuming they might not have much truth. I guess my question is that after 5 months of consistently hooking up with one person, but nothing serious coming out of it yet, can it turn into being more than sex? And from a guy's perspective, what is a good way to bring up getting out of this just sex relationship?

Bootycall No More Betch

Wow. Just be like “hey, this is obviously a lot of fun, but I’m getting to the point where I’m looking to be in a real relationship and I don’t know if you’re up for that.” Then he’ll either say “totally, me too” or “nope, I’m not” and then you can act accordingly and get on with your lives.


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