Why Doesn’t Texting First Ever Work For Me? Ask A Pro

Email Head Pro your most pressing dating conundrums at headpro@betches.com. He will probably roll his eyes, but you won’t know that, will you?

Dear Head Pro,

Is it ever advisable to text a guy first? My thinking goes: If I text first, how can I suss out his intentions and get to that sexy place where he is in the driver’s seat and I’m being “courted” for lack of a better word?

Typical scenario: A guy is obviously hitting on me the whole night. I may or may not kiss him, depends. He takes my number, he may or may not text to see if I got home safe, depends. Days go by and no contact. If I really liked him, is it ever advisable for me to text first?

Thanks in advance!

I promise I’m not a princess

I can’t tell if you’re talking about texting someone for the first time ever, or being the first one to send a text on a given day to someone you’re already in contact with. If it’s the former, it’s a no. The only reason guys text first is because we’re expected to. Otherwise, we wouldn’t do it because it sucks. It gives the person on the receiving end all the power. Guys accept that they have to be the ones to initiate, so if you do it he’s going to assume you’re trying to lure him to a sex party that ends with his death.

If it’s the latter, yes of course you can text first. If that’s your understanding of “texting first,” I feel you’ve left in your wake a slew of confused guys. Like, if he texts to make sure you got home ok, how would it be “texting first” to reply that you did, the next morning? Like, guys understand text etiquette too, and they sure as shit aren’t going to pull the dreaded double-text.

In general, don’t waste too much time trying to determine a guy’s intentions from a text. Like, if he’s texting you, he wants to fuck you. He may want to do more or less in the future, but no one was ever proven wrong by operating on that premise.


Dear Head Pro,

I’ve been seeing this guy for almost a year now. We met through mutual college friends and have always been more friendly than flirty, casual and non-exclusive. I’ve never gotten too jealous because we are pretty transparent about our other “ties,” since I’m bi and he is a “likes to explore” (a.k.a we’ve had a few 3/4somes) kind of feminist.

Lately things have been getting pretty intense, despite us both saying that we don’t believe in monogamous, possessive, co-dependent relationships. We’re both pretty independent and only see each other 1-2 times a week, but recently he’s been inviting me out with his friends for dinner and turning up the PDA 10 fold. I’m not sure how to approach a conversation because I don’t want to complicate things too much, but I do want to acknowledge that we have some kind of feelings for each other.

I also feel like part of why he acts so affectionate towards me is because I’m so chill [420 friendly ect.] and I’m sure he likes that I like girls too—so idk if he thinks I’m just super casual about PDA and friend-meeting and stuff cuz I’m a ~free spirit~ (barf) but I already told him I’m not super casual about affection and I’ve had only one serious and toxic relationship back in high school.

Am I crazy for thinking he wants something more? He definitely knows I’m down for something loosely defined and open.

Or is he just playing the field and being extra cuddly because I’m clearly not adding any strings to attach us anyway.

Although he tries to give off the vibe that he is a ‘free love’ kinda guy, I feel like he’s more of a commitment-phobe. So how do I approach this?

I’m not trying to scare him off cuz I’m focused on my career right now and could really use the weekly lay regardless, but I wouldn’t mind being more open about my feelings. Idk. This is some millennial shit my mom can’t help me with. 

He invited me to go out of town with him and his friends for a weekend but I sense some hesitation from him as well. Like, I’m not sure I want to berate him with some girly feelings, but I feel like going on a mini vaca and not knowing what he really thinks of me is a little nerve-racking.

Help me, Head Pro. Thankz


Dating Don Draper

Well, let’s start with the obvious, being that even if he wants something approaching a normal relationship, it would be awkward after you all mutually disavowed “monogamous, possessive, co-dependent relationships.” Christ, just copying and pasting that makes me want to go back and change my vote to Trump. But yeah, that makes broaching the subject inherently difficult.

There’s so much shit going on in here that it’s hard to really know for sure, but generally speaking if a guy’s actions and words diverge, you follow the actions. Like, if a guy were saying he loved you and wanted to marry you and have babies but never wanted to be seen together in public, you wouldn’t believe what he said, right?

Same here (I think). He talks like he’s some kind of Dionysian Che Guevara, but more likely he’s just a dude who appreciates your chill vibez, likes you, likes fucking you and, yeah, is very interested in the whole bi thing.

I think you take advantage of his performative progressivism and be the one to start the conversation. I agree that being invited on a trip is a big enough deal where the uncertainty would be an unpleasant, nagging thought. Just say something to the effect of “I want to go on this trip with you, but should we maybe talk a little about where we are, since it’s been a while?”

Maybe smoke some weed first.

Email Head Pro your most pressing dating conundrums at headpro@betches.com. He will probably roll his eyes, but you won’t know that, will you?


More amazing sh*t

Best from Shop Betches