Ask a Pro: What Are The Rules of Getting Engaged?

By The Head Pro

Head Pro,

Not necessarily an advice question per se, but I'd like to get your opinion on proposals. How surprised do most people want their s.o. to be?

The idea of a complete surprise seems a little bit crazy, but I wouldn't want to know all the details either. Just looking for some manly views on this.

-I have no bad pun for a name, plus my name's in my email…

Dear Phoning it In,

You do realize that, like, most people’s names are in their email addresses, right? That’s usually how that works. Unless you created your email address when you were 14 and somehow still use it, what else would it be? Actually, that’s a good question - what would an email address that’s unrelated to your name but still acceptable for adult use look like? Discuss.

Anyhow, yeah, I think a complete and utter surprise proposal would be dicey, if not hard to pull off. It could work if you’ve been together a really long time, because Lord knows she was probably expecting it yesterday. With a shorter courtship, I think there’s a general discussion/agreement as to the mutual desire to get married. The time and place can still be a secret, but in general as a guy I’d want to at least know that she’s not opposed to the idea. That said, I think a lot of people nowadays engage (haha) in wayyy to much mitigation on that front.

For instance, I think “ring shopping” together is tacky as fuck. I’ve even heard of couples pooling resources so they can blow entirely too much money on the “perfect” ring. Just, no. Not everything has to be a coed activity. Though it was assumed engagement rings were once a signifier of “ownership” on the part of the groom, scholars dispute that now meaning they are and likely always have been simple gestures of commitment. That’s why when the guy goes shopping, it’s his job to pick something that he believes suits the girl and reflects who she is and what she means to him. Turning it into a joint brainstorming session only further cheapens what amounts amounts to little more than symbolism to begin with.

TL;DR - Having at least an inkling of the proposal isn’t a bad thing; don’t go ring shopping.

At least you didn't use "Dazed and Confused,"

Head Pro

Dear Head Pro,

I have a question that has been plaguing me for the past few months. I did the whole one-night-stand thing a few times, and then decided it wasn't something I wanted to continue doing. I've met 2 or 3 guys who I have hit it off with and they have all said things like this to me: "you're exactly my type", "it seems like you just get me", "I've never met a girl who has a sense of humour like you" blah blah blah. Then, when they tell me they want to take me home, I say no and this prompts them to tell me how much hotter this makes me and how much they respect me. BUT, i'm having this issue where when I ask them "when can I see you again" after some flirting, they get all strange and say something non-committal like "whenever you're in the city, give me a shout".

So my question is, what's the point of saying a line like that to a girl when it's not actually true. Is this some men's way of trying even harder to get the girl to come home, since he now "respects her"? And does this actually work? Or am I some kind of strange Unicorn who doesn't fall for these lines. How do I tell the difference between the ones who actually do respect me, and the ones who don't.

Ps. It's not like I am asking these bros to be my boyfriend and get married. I literally just want to see them more than once before we have casual sex.

Thanks Head Pro,

Unicorn Betch.

Dear Unicorn Betch,

Ah, the rarest betch of them all! You kind of answered your own question, to a degree - when you shut down their unsubstantiated word-vomit of random compliments, their assumption is that the REAL barrier to some same-night lovin is “respect.” And in a sense, they aren’t entirely lying. Being a challenge to someone does tend to make you abstractly more attractive. It’s just that by saying that, they aren’t giving your intelligence any more credit than they were when they were spewing baseless compliments at you. If anything they’re giving it less: While a guy can reasonably observe beauty or potential compatibility pretty quickly, it’s silly to assume he can grow to “respect” you in such a short time. “Not fucking me within hours of meeting me” is a pretty low bar for respect.

Does it work? Sure, the same way whipping your dick out onto the bar can “work,” sometimes. The kinds of guys who get with a lot of girls, while not the savants some people imagine them to be, are at least smart enough to know that lines like that are tired and trite for a reason. If you want to know if a guy actually respects you, you wait and let him demonstrate that. When you decline his invite to poundtown, he’ll say “ok, cool, let me get your number.” What they won’t do is try to pantomime respect by stomping their feet and yelling it and maybe singing that Aretha Franklin song. If you think about it, implying that a declaration of “respect” should lead to sex is just a more subtle version of the fedora-wearing crowd’s “I’m nice to her, so she should fuck me” mantra.

In a way, asking “when can I see you again” is kind of like saying “you’re going to have to put in work if you want to hit this,” so thats not really necessary either. I mean, asking the drunk guy who just propositioned you for a sex at 4 a.m. to make future plans with you on the spot isn’t any more reasonable that his initial proposal. Just exchange numbers, text each other some “good night” pleasantries, and see where things go.

Respectful Kisses,

Head Pro




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