When Do You Tell A Woman You Like Her?

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When Do You Tell A Woman You Like Her?

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Hi Doc!

How do allosexual folks who relate to some elements of demisexuality date in an honest way without beating around the bush or waiting too long?

Without getting too lost in labels, I am 30 year old male on the neurodiverse spectrum (both ADHD and ASD) and I relate to labels such as demisexuality, non-monogamously wired (but not sure if polyamory specifically is right for me at this time in my life), somewhere on the queer spectrum but attracted to women and non-binary folks more on the femme side, and going through a lot of questions moving forward after the pandemic subsides again. I think both he/they pronouns feel comfortable because I have a lot of different traits that don’t fit neatly in the category of male gender.

I can be very attracted to folks within an eyeshot of first meeting them, or I can also develop attraction after getting to know someone as a friend over the course of months or a year or two. I read a lot of authenticity/honesty/vulnerability psychology and dating advice, and a lot of men’s coaches/counsellors, etc. seem to advocate for being completely honest about my attraction for someone upfront as soon as possible such that I demonstrate my honesty without being seen as someone fearful or distrustful, and to avoid the “Friend Zone” (which I am well educated and aware that the label is unhealthy and mired in entitlement or misunderstandings of how relationships work).

But the problem with all that advice is I’m not always sure when I’m comfortable expressing my sexual desire for someone, after weighing the details of who they are, whether I’m compatible in the ways I want to be with them, their emotional and communication receptiveness, or when they themselves are at the right time in their life to sexually or romantically connect. As an example, a friend that I met a few years ago who I was initially attracted to but in a relationship at the time is now going through a messy breakup and she has expressed lots of interest in spending time with me, inviting me to quarantine at her place or even live with her after moving to the new city she is now residing in, etc. Since she is going through a lot in life, I want to be a good and supportive friend who respects boundaries, while at the same time I am anxious about when to express how I feel towards her. I am afraid of whether she will be comfortable with how late I have introduced this vulnerability.

Anyhoo, I am also caught up in trying to find the right balance of figuring out what is my ADHD-related impulsivity/desire for novelty and what parts of my sexual connection are healthy or based on neediness or biological quirks that come with neurodiversity and having dopamine systems that function differently and etc., Adding the layer of RSD on top of that, I struggle with a lifetime of self-sabotage and internal dialogue that tells me “who am I to ask for what I want” or “get over it, stop wanting sex so much, move on with your life and be grateful you even have friends”. I don’t want to sexually connect with just anyone, I really want to prioritize meaningful and quality connections based on my values and etc. that include sex and fun.

Sincerely,
Rosemary Bush (my potential drag name that I have “claimed” if I ever explore that realm)

Before we get to your question, RB, there’re a couple of terms that we should probably define for folks — in no small part because they’re going to be relevant to your question. First is demisexuality, which is an orientation where folks only start to feel sexual attraction after forming an emotional bond to a person. Next is RSD — that is, Rejection Sensitive Dysphoria. This is something that crops up a lot in concert with conditions like ADHD and anxiety disorders. Rejection Sensitive Dysphoria is a condition of heightened emotional response to any sense of rejection — whether real, suggested or imagined. While nobody likes being rejected or feeling as though they have been or are going to be rejected, for most folks it’s just unpleasant. For folks who have RSD, it’s a frequently overwhelming reaction that could be akin to an anxiety disorder or phobia. In effect, it’s like someone took the usual feeing of rejection, dialed it up from a 5 to 12 and then snapped the knob off.

I bring these up because… well, I think in your race to label yourself, I think you may be misattributing some of the issues you’re having. Take how you relate to demisexuality. I’m not entirely sure what you mean by this, since, quite frankly, you don’t seem to be using the term correctly. In your next paragraph, you say “I can be very attracted to folks within an eyeshot of first meeting them”. This is the opposite of demisexuality; demisexuals’ sense of attraction is a slow burn, not a lust-at-first-sight kind of situation. If you’re getting the hots for folks right off the bat as well as developing over time, that’s not demisexuality, that’s allosexuality — that is, the commonly accepted idea of how people develop sexual attraction for others.

But honestly, I’m wondering if, in applying all of these labels to yourself, you’re more trying to live up to the label in hopes that it’ll change things for you, rather than understanding yourself and getting both familiar and comfortable with yourself and your sexuality. It seems more like you’re dealing with RSD and a general discomfort with your own desires and desirability.

Case in point: you mention that you have to do complex analysis of your interest in someone before you feel comfortable making a move. In fact, you list so many things that you supposedly consider that I’m wondering if you’re keeping dossiers on folks you find sexy. I mean, trying to measure their communication receptiveness or readiness to sexually connect? This sounds more like trying to draw up a psychological profile of a target rather than an attempt to get a date.

But it’s that very complexity that makes me think that this is less about “figuring out when to tell someone I like them” and more of a delaying tactic. You can’t just ask them out on a date, you need to figure out all of these complex, interacting systems before you can even begin to express interest in someone. This, to me, comes across as avoidant behavior, a sort of anxiety self-defense mechanism that can be dressed up in analysis drag. It’s the sort of thing that can seem like an understandable delay — you’re just trying to figure out if she’s right for you! — but one that ultimately means that you “can’t” make your move yet. Similarly, trying to figure out all these variables — where is she in her emotional journey,  how receptive is she to communication right now — are about trying to guarantee that you won’t get rejected; if you can just double and triple check the math, you can make sure you’ve got a 99% chance of success!

Except you can’t. The point of this exercise isn’t to confirm compatibility and prevent getting rejected, it’s a permission structure that allows you to avoid doing the scary thing: actually making yourself vulnerable, putting your interest out there and asking her on a date. By telling yourself that you’re just doing your due diligence, you are giving yourself permission to avoid doing the things that you’re worried about. After all, as long as you don’t actually get rejected, then you can keep the dream of a relationship with them alive. Putting yourself out there, on the other hand, means you risk getting rejected and being hurt. And since you’re dealing with RSD, anything that smacks of rejection or the potential of getting rejected is to be avoided at all costs. Even if that rejection is strictly in your head. So you have, for all intents and purposes, created a system designed to give you analysis paralysis and — in the process — “save” you from the risk of being rejected.

Trust me: I have been there, done that and created all sorts of elaborate reasons why I couldn’t just ask someone out… yet. Game, as they say, recognizes game.

The problem with this psychic self-defense is that it ultimately means you miss out on… well, pretty much everything. You’ve set yourself up with a catch-22. You put yourself in a position where you don’t feel comfortable expressing interest in someone early on, but then feel like you can’t express interest in them later because it’s been too long. So either there’s a very narrow window of opportunity that you just keep missing by THIS much… or you’re just setting yourself up for a “can’t do it today, doing it tomorrow will be too late” situation.

Worse, it means you’re missing out on opportunities that are virtually being dropped in your lap. Your friend is telling you that she wants a closer relationship with you — maybe romantic, maybe not — and you’re waffling over whether you can/should tell her you like her. And while I understand the fear of ruining the friendship, someone who’s asked you to quarantine with them or even just move in with them isn’t likely to be thrown by finding out that you’ve got a thing for them.

You’re also creating false dichotomies for yourself. You aren’t stuck between “tell them you’ve been in love with them from day one” and “never say a word”. Nor, for that matter, do you need to give these anguished declarations of love; in fact those tend to get a worse result than just, y’know, asking them out on a date. Part of the problem with “confessing your feelings” is that it puts the onus on them to do something with those feelings. That’s a lot to drop on someone all at once. They may need some time to figure out how they feel, but the confession comes with the added pressure of having to define exactly what this relationship is going to be.

In general, you’d be better off just asking them out on a date; the “I’m interested in you” is implied by the “date” part of the equation. Asking them on a date, however, is also a much easier lift than a full-bore confession. It’s much easier to decide if you want to go on a date with someone and just see where things go than it is to have to decide, then and there, if you’re interested in a relationship with someone. A date can lead to a relationship, but it also allows everyone involved to ease themselves into it, rather than having to jump in with both feet.

But none of that can happen if you don’t accept the risk of rejection in the first place.

Part of why people say you should express interest (i.e. ask someone on a date) early on is because you’re trying to avoid The Friend Zone, as well as avoiding Nice Guy behavior, sure… but it’s also intended to keep you from locking yourself into analysis paralysis. If you spend weeks or months trying to figure out the precise right time and manner to ask someone out, then you end up building the importance of this relationship up ion your head. Because you spend so much time thinking about it, you end up emotionally over-investing in them and their response. Now whether they say “yes” or “no thanks” is a matter of dire importance that only gets even more momentous as you wait. Making your move earlier, rather than later, means that you don’t have as much time to build things up and psych yourself out further.

So, you need to stop waffling and trying to run the numbers, muscle up and just ask people out on dates when you know you’re interested in them. It doesn’t require a confession or an explanation of how long you’ve had feelings for them. All you need to say is “hey, I love our friendship, but recently I’ve been interested in more. If you’re up for it, I’d love to take you out on a date.”

Now, I freely admit: the RSD can make this harder. Getting your RSD under control is going to be important. But rather than trying to will yourself through it, I’d suggest working around it. Cognitive behavioral therapy goes a long way towards helping you deal with those intrusive thoughts and anxieties and talking yourself down off the metaphorical ledge. So if you want to be able to actually act on your interest in others, quit trying to work the angles and get yourself to a therapist. That’ll help you more than all the labels and all the calculations in the world.

Good luck.


Hello Doctor

I’m at an awkward part of my life at 26 I’m at a point where I don’t have any friends. My social circle is empty really and dating potential is in the same place. My issue is how do I meet single women and people in general?

I’ve tried to pursue my interest but it hasn’t gone anywhere most of my hobbies are solo pursuits because I’ve had to develop solo activities and maybe it’s COVID maybe it my area but the ability to join something where people meet up in groups isn’t really happening at the moment and I know this extends to my dating ability and opportunities. I’ve never been in a relationship and as I get older the ability to make friends and find single women just seems to be getting harder people are busy with their lives and I kind of feel left behind.

Now I have tried to do things to meet people and women I’ve tried online dating but we all know that it’s not exactly easy to meet people online dating. I’ve tried joining a salsa class ,which is big step for me, but it was just full of creepy guys looking for women and our teacher. I guess I’m at a point where I don’t know how i can possibly increase my dating potential and my social networking in general but I’m at a loss.

Sore Thumb

You’re in luck, ST: you can solve both your social woes at the same time. By making a point of meeting new people and building your social circle, you increase your opportunities to meet and date incredible women. Having more friends in your life and spending time with them helps bring more people in your life in general… and that includes the kinds of women you like to date.

The problem you’re having, though, is that you’re cutting yourself off at the knees. You’ve written off a lot of opportunities before you’ve even really given them a chance to succeed. Yes, COVID makes things that much harder, but “difficult” isn’t the same as “impossible.” What you need to do is very simple: go where Your People are. This is why I tell people to pursue their passions, interests and hobbies; knowing what you’re into and what the people you want to be friends with are into makes it easier to identify the places where they’re likely to spend time. This includes passions or interests that are supposedly solitary pursuits. While yes, there’re activities and hobbies that one usually does on one’s own, that doesn’t mean that you can’t meet other folks who’re into them as well. The trick is to apply a little lateral thinking.

Let’s say you’re into gardening. Yes, that’s usually something folks do on their own. However, there’re a ton of opportunities to meet other folks in your area who’re into gardening. There’re events, lectures and classes, there’re local online communities — especially on Facebook or Reddit — and so on. Folks who like reading have book clubs, author signings and readings, writing classes and so on. Part of finding Your People means thinking a little past “well, I do this thing by myself, so I can’t meet other people that way” and, instead, looking towards activities, groups or events that’re related to those interests.

Part of what helps is to go online and find out what’s around you. A lot of times, we tend to assume that there’re fewer folks in our area who’re into X, Y or Z because we never happened across them. But that doesn’t mean they don’t exist; it just means that waiting for opportunities to fall into your lap is a bad way to find out what’s available to you. Use social media, Reddit and the other resources available to you to find out more about what’s going on in your town — or even within a reasonable distance — that you may not have ever known about.

Now, the other part of the problem isn’t just finding the right activities or classes, it’s going about meeting people the right way. You’ve encountered one of the problems: sketchy dudes who’re cruising the classes and meetups like horny sharks. Those are the guys who chase women away from groups they enjoy or meetups they might otherwise keep going to. You don’t want to be one of them, obviously, but how do you avoid it?

The answer’s simple: you don’t go to these classes just to meet women. You go to be social and meet people, in general. If you’re only talking to women, especially only to women you find attractive, then yeah, people’re going to think you’re a sketchy dude out to do some sketchy shit, do dah, do dah. You don’t want to show up and just hit on folks. You want to go, enjoy the group for its stated purpose and become a regular. As you spend more time there and get established,  you become more familiar and — by extension — more liked within the group. Exposure breeds familiarity and familiarity breeds affection… and attraction. Propinquity is a powerful part of building attraction and affection to others, so becoming an established member of the group goes a very long way towards helping you fulfill your goals.

This, incidentally, is why you want to take classes or join groups that you’re genuinely interested in. By showing to others that you’re there because you legitimately want to learn or take part, you’re building trust and demonstrating that you’re not one of the creepers hoping to use the class as their personal sex ATM. Plus: passion is attractive and shared passion can be magnetic.

Another thing to keep in mind: sometimes you need to look a little further afield than the most obvious choice. Yeah, all the sketchy dudes are at the salsa classes.  But have you checked out, say, pilates classes or hip hop dancing or other classes and groups that are related  to the things you’re into? Doing a little more investigation helps you figure out where the people are, especially where there’re likely to be more women, and  especially women who’re more your type. However, again: you don’twant to be the horny guy who shows up to class; you want to make a point of going to these classes — or what-have-you — to learn and participate. That doesn’t mean you don’t talk to people. You should be social and get to know folks and build connections with them. What you don’t want to do is immediately start angling for dates. Instead, get to  know people, become a familiar and trusted face and build that trust and familiarity. As you get to know people… well, if you find out over time that someone’s your type and you feel like the two of you’ve caught a vibe, then you can ask them out  on a date. It’s the dudes who make it clear that they’re looking for human-shaped Fleshlights and aren’t interested in women as people who creep everybody out.

And one more thing: just as you may want to look a little further afield when trying to find classes or groups, you should look a couple steps beyond just who’s attending those classes or groups. Part of what trips people up is they see the folks at, say, the sushi-making class and either don’t see any single, available or attractive women and give the whole exercise up. This is a short-sighted mistake. The key to going to these groups and classes is to meet people in general and make friends. Making friends with folks brings them into your social circle… but it also gives you access to theirs. You may not be meeting the women you want to date at your social dancing class, but you very well may meet the folks who’ll introduce you to them later on.

Good luck.

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