When Is It Time To STOP Asking Someone Out?

When Is It Time To STOP Asking Someone Out?

Estimated reading time: 14 minutes

Doc, can you tell me what the hell is going on here?

Quick backstory before I get to the important parts: I have a solid network of friends and friends of friends that I hang out with regularly, and most of us tend to run in the same circles, so I will frequently see people I don’t know at a lot of different parties or kickbacks. The circles overlap, but not perfectly, so there’s almost always people drifting in and out of the groups and a lot of “wait, I thought you knew them” conversations. So there’s a lot of turn-over in terms of strangers as friends of friends of friends come and go and people break up.

One night several weeks ago, a bunch of us go to a bar to watch a game, and I meet a woman that I’m going to call Amanda. Amanda is a little older than me (mid to late 30s if I had to guess) which I’m not mad about, incredible legs, a ask-no-pardon-take-no-shit level of sass and smoking hot with actual smoking. I have never wanted to be a cigarette more in my life. The sort of person who would smile and deliver cutting replies to the guys who would hit on her that they would only realize later were put-downs. As someone who is into women who will smack me around a bit (verbally, but I wouldn’t say no to physically too if that’s her thing), I had to meet her. Some of my friends clearly knew her, so I went up, bummed a light and started talking.

Long story short, we get along like a house on fire. I’m flirting, she negs, I neg back, she threatens to spank me like the naughty boy I am, I ask if she’ll dress like my 8th grade history teacher when she does, she laughs, we trade numbers. I figure I’m in with a chance.

Since we have overlapping networks, I see her multiple times at parties, cookouts and watch parties. When we’re in the same room together, it’s electric. The flirting is explicit. I don’t mean “I think she’s flirting do you think she’s flirting”, I mean that after one dinner party when Amanda had left and I was helping clean up, a good friend came up and asked why I was still here. When I asked why, she said that she thought that Amanda and I were about to either tear each other’s clothes or face off. Apparently the sexual tension was visible two apartments over. Dogs howling, flowers perking up, glasses steaming, electrical appliances shorting out, you name it.  

Texting is similar. If I’m staying home while her slice of the network are out doing something, I get texts showing her in her girls-night outfit and a pouty face asking why I’m not there. When we are just texting, there’s banter. There’s flirting. There’re implied promises and threats involving rulers, paddles and very very red asses. Mostly mine. Still not mad about it.

What there isn’t is action. I ask Amanda out and I get vague promises, put-offs and “ask me on Friday”. I invite her for dinner, drinks, art walks, jazz nights, at one point a round of hitting golf balls when my boss booked a company party at a driving range with a bar attached to it, just to see if that would do the trick. Every time: put-offs, last minute “oh I can’t’s,” told she’s double booked.

After the first couple brush offs, I figure she’s either not into me or there’s someone else. I even ask if her boyfriend objects to my talking to her like this, and she says “who says I have a boyfriend?” I ask her straight up if she’s seeing someone and she doesn’t give me a straight answer. Hot, but frustrating is the name of the game and I know when someone’s just not feeling it. That’s great, that’s fine, I’m a big boy in my big boy suit, I can take a hint.

But every time I back off or Amanda sees me talking to someone else, it’s game on again. My phone starts to blow up with pics that are spicier and boobier than her usual fit checks, she makes a point of coming over when I’m having a smoke break and talking like Jessica Rabbit decided to be a soft-dom. I figure maybe I’ve misread things so I flirt, she flirts back, I ask her on a date, she does the same put-off routine. I back off and suddenly the threats to put me over her knee and teach me the lesson my mommy should’ve are back and I’m both hard AND frustrated because I really wish she hadn’t said mommy, that weirds me out. How is a guy supposed to respond to that without a lot of awkward conversations with my therapist afterwards?

Oh and also I still can’t nail her down on an actual date. I’ve told her to take ME out on a date, even said “ok, enough with the games, wanna just go back to my place and smack me around?” in case the problem was that she didn’t do dates or something. Same response: lot of vague promises that aren’t actual promises, a lot of “check back in with me” and I’m back on Saturday night with no plans and no fun bruises to explain at the gym.

Doc, at this point I am throwing my hands up with the hair I’m pulling out in frustration. I have no idea how to take any of this, and I’m running out of hair. She’s into me, I’m into her, I’ve tried everything from subtle to romantic to blatant, and nothing happens. If I back off, then in comes the freight train of texts and interest.

I like the game as much as the next guy who also likes games but at this point I don’t know what the damn rules are. I’m hot for her to the point of dyin, but I’m also getting tired of tryin. Is there a way to cut through the bull and get to the meat of whats going on or do I just give up and ignore things when I get the next series of texts? At this point I think I’d be ok with just answers, even if it doesn’t come with a paddling or a putdown. What do I do?

Smack My Ass And Call me Susan

There’s a part of me that’s wondering if we know the same person, SMACMS, because that sounds a lot like the dynamic I experienced with a woman back in my PUA days. To the point that I’m a little suss, if I’m being honest.

But as per my policy, I’m willing to take this at face value, because not only do I think there’s a lot to learn here, but because I’m going to give you advice that I wish someone had given me back when I spent all my times (yes, plural) beating my head against the wall of wanting to get with someone who always seemed to keep herself just out of reach.

It sounds like she’s playing games with you. The question at this point isn’t “what game”, the question is “why are you still playing?”

One of the most important lessons someone on the dating scene needs to learn is that it takes two to tango; if you’re in a situation that seems untenable, the one thing that’s keeping you there is you. This is true whether you’re feeling like you’re stuck in The Friend Zone* or you’re dealing with someone playing a game of “go away a little closer”. No matter what game you or they may be playing, there comes a point where the only way to win is not to play. If you’re continuing to play… that’s ultimately on you, and you should be asking yourself why.   

*There is no Friend Zone, there are just people who don’t want to fuck or date you.

I’m not going to get into a lot of analysis and speculation about what Amanda is doing, because at the end of it all, it’s a fairly pointless discussion. Maybe she’s got reasons why she she’s not able to go on a date. Maybe she thinks you’re not serious and you’re just playing around. It could be that she likes having power over you and enjoys the thrill of having your attention. Maybe she’s waiting to see how long you’ll keep at it before giving up. Hell, maybe she just enjoys the flirting and getting you riled up and then takes that energy home and proceeds to see whether she and her baboo can bust the dry wall with the headboard.

The details ultimately don’t matter if it all leads to the same place. She likes flirting with you, she likes getting a rise out of you (er, as it were), but that seems to be the end of it. Figuring out what game she’s playing isn’t going to make a difference if the end result is the status quo; the answers aren’t going to bring you meaningful closure, not when you’re still trying to play.

So let me ask you a question: are you enjoying the dynamic as it is? If you knew with 100% certainty that this is all there will be between the two of you, would you still want to keep at it? Or are you throwing time and attention and effort at trying to hook up with someone that you could be using to meet someone else?

You don’t say if you’ve gone out with anyone else, if you’re still trying to meet other people or if she’s the only person you’re trying to hook up with, but it sounds to me like you’ve zeroed in on her to the point of ignoring any other possibility. And hey, if you’re cool with that, more power to you, chief. It’s fine if the frustration works for you, but I think there comes a point where you need to step away. For real, not just in hopes that she’ll finally say “ok, you win” and meet up for ass-beating you’ve been hoping for.

You can keep trying, sure. You can try to crack the code. Maybe it’ll even work. But speaking as someone who’s been there and done that and even succeeded, I will tell you that I’ve seen the future and if you’re focusing on trying to hook up with Amanda to the exclusion of everyone else… well, I think you’re going to end up being more disappointed than if she riles you up before poking you in the Opedipal complex again.

If you really want, you can try to get her alone, drop the bratty sub routine and ask her, flat out, what she wants from all of this. Lay your cards on the table, ask to see her hand and see whether that hand is  going to leave a mark on them cheeks. Maybe using your words will break through and she’ll finally tell you to meet her after class for detention. But I’d suspect the likelier outcome is that you get to give yourself some closure.

If you’re not enjoying the game for the sake of the game, then it’s time to stop playing, even when she’s trying to tempt you back in. The game’s only fun until it isn’t any more. And if the problem is that she wants you to play it the right way… well, play stupid games, win stupid prizes.

She’s made her move. Now it’s time to make yours.

Good luck.

Dear Dr. NerdLove: I am 22, ADHD for sure but probably AuDHD, and two very short-term relationships. Every time I have a date with someone I like, I overthink. I second guesss myself, I read and reread the signs, I am looking for subtext when I don’t even know if there is subtext. Every single time, I feel like there’s something going on that I’m missing and I can’t figure it out.

I know it makes me too intense. My last girlfriends both told me that they broke up with me because I kept asking what was wrong or needing them to tell me everything was ok. I hate it, btu I can’t stop it. How do I turn my brain off and stop looking for trouble?

Shut Up Brain Before I Poke You With A Q-Tip

You say up at the top that you have ADHD, SUBBPAQ; are you actually in treatment for it?

I ask, because what you describe sounds like symptoms of rejection-sensitive dysphoria, which tends to come as part of the neurodivergence combo platter. RSD is co-morbid with a wide range of neurodivergent conditions – including, but not limited to borderline personality disorder, ADHD and autism. The best way I can describe it is that it’s a fear of rejection, taking the anxiety that you’ve messed up a relationship in some nebulous way, turning it up to 11 and then snapping the dial off.

If you aren’t treating your ADHD, if you’re working from a self-diagnosis rather than talking to a medical professional (instead a loudmouth with a blog – remember, Dr. NerdLove is not a real doctor), then I highly recommend that you do. I am one of the unlucky bastards whose ADHD came with a side of RSD, and finding the right medication and dosage did wonders for making my jerkbrain shut the hell up.

If you aren’t – whether it’s “aren’t yet”, or there’re reasons why you can’t seek treatment – then what I would suggest is focusing less on the thoughts themselves and more how you relate to them. RSD is a form of anxiety, and at the end of the day, anxieties are a form of self-defense. Your brain is trying to protect you from “danger”; the problem is, that it’s trying to protect you whether there’s danger or not. It’s a little like an Aussie Shepherd without a job; it’s keyed up, so it’s barking constantly, chewing on your shoes and ripping up the furniture.

Functionally speaking, what this means is that you’re getting a lot of false positives. You’re getting signs of danger where there isn’t any, because your brain is determined to find them regardless. It plays on the worry that you’re missing something, and so you start looking for what it could possibly be. And because confirmation bias is part of the BIOS that runs the human operating system, it’s going to find them if it has to invent them out of whole cloth.

So the first thing I would suggest is working on your relationship with your thoughts. Mindfulness meditation is a great way to not only recognize anxiety thoughts when they happen, but to learn how to tell your brain “shhhhhh”. I would recommend trying a guided course on meditation – apps like Headspace and Calm both have lessons as well as daily guided meditations. Learning how to notice that you’re having thoughts without judgement and to turn your attention away is invaluable.

I would also suggest supplementing it with cognitive behavioral exercises. CBT is especially good at treating intrusive thoughts and anxiety; the point is to explore and dig into what those thought chains are saying, to recognize triggers and how to change the way you respond to them and channel your attention in positive and productive directions. There are a number of self-guided exercises that you can find online, but – as with all things mental-health related online, the quality can vary, especially with amount of LLM slop out there. I’d recommend starting with an organization like MoodGym; otherwise, double and triple check the credentials of ones you find on YouTube or Amazon.

Do not – and I can’t emphasize this enough – ask ChatGPT, Claude or Grok. It won’t help, and it will only make it worse. 

In a pinch, I would recommend taking an attitude that if someone hasn’t told you that they’re upset with you, you should assume that everything is fine. You want to assume that people are being up front with you and everything is as it appears, rather than being fraught with hidden meaning and signals and secret messages that even the Victorians would think is a bit much.  

Yes, I know that your anxiety is screaming at you that it absolutely isn’t, but trusting your gut is only worthwhile if your gut is trustworthy… which right now, it isn’t. Just because you know you may not be good at picking up signals or subtext doesn’t mean that there is subtext to be picked up. The fact that you’re not good at seeing them or interpreting them when you do should be the single biggest reason to question whether you’re interpreting that subtext correctly… or if there’s any to be interpreted in the first place. Most of the time, what you think you’re seeing has absolutely nothing to do with you, and you’re often picking up on completely unrelated details. I’ve seen a hell of a lot of unnecessary fights happen because one person read “my partner is upset at me” into “I haven’t eaten since breakfast and my blood sugar has dropped through the floor.”

Starting from a position of “if someone doesn’t tell me there’s a problem, there isn’t one” will cut through a lot of the ways you’ll set yourself on a doomspiral, which will give you some breathing room while you wait for the feelings to chill out and go away.

And they will go away. It’s actually hard to maintain a particular mood or emotion if you’re not reinforcing it; if you leave things alone and direct your active attention elsewhere, the feelings tend to fade into the background and dissipate – often in 90 seconds or less. This, incidentally, is part of why folks recommend counting to 10 or walking it off when you’re angry; it’s a way of forcing you to give yourself time for the moment to pass instead of lashing out or acting impulsively.

But – again, speaking from experience here – if it is RSD, then medication is going to be the best course of action. I’m a big believer of better living through chemistry and getting my “brain work gooder” meds was a goddamn revelation – like putting noise-reducing headphones on in a boisterous restaurant.

In the meantime, though: if you know you’re overthinking, then the goal should be to think less. Do the exercises that will help you get a handle on your brainmeats and you’ll be in a better position to give that border collie in your brain the enrichment it needs so that it quits ripping your emotional couch to shreds.

Good luck.

Leave a Reply

Your email address will not be published. Required fields are marked *