These are the rules I follow in the realm of dating. Which ones should I keep, and which should I discard?

I’ll just put them in bullet points for simplicity’s sake:

* Asking a woman out means projecting your feelings of attraction onto her, and implies an expectation that she will reciprocate. It is therefore essential that you have the social awareness necessary to gauge whether or not she might be interested, and to refrain from asking somebody out in instances where you don’t at least feel somewhat assured that you are likely to get a “yes”.

* It is not flattering for women to have someone express attraction towards them when the feeling is not reciprocated. It is uncomfortable, objectifying, and indicative of underlying feelings of male entitlement. **You do not have a right to make someone feel uncomfortable, and you have a moral obligation to actively avoid overstepping boundaries.**

* **Always assume that a woman is not attracted to you unless she explicitly tells you that she is.** Giving you a compliment is ***not*** expressing attraction. Playfully teasing you is ***not*** expressing attraction. The only reliable indication of someone feeling attracted to you is if they *very explicitly* say so. Rule of thumb: if you’re not sure if they’re interested, they’re not. Most people instinctively “know” when to take things further, when flirting with someone is welcome, etc. If you don’t know whether or not it’s appropriate, assume that it is not.

* A “yes” is fleeting, subject to change without notice and for no discernable reason at all. A “no”, on the other hand, is **FINAL**. “No” means *never*—If someone is not attracted to you from the outset, *there is absolutely nothing you can say or do to ever change that.* No amount of time, effort, or “seduction” will get them to like you back. Waiting for them to change their mind is disrespecting their agency and their feelings. Move on.

* You don’t just ask somebody out on a date—you get to know them first, you ask them out at the right place and time, and you gauge the situation well enough to know when doing so is appropriate. First, you need to befriend them. Wait until you have gotten to know that person for a minimum of 3-4 weeks, but a maximum of 2-3 months (some leeway is allowed here, but these are general guidelines). Pay close attention to their intonation and body language when talking to them. If you sense that they might be interested, ask them out in a public setting where there’s few people around to notice—thereby alleviating any pressure that might be put on them from others—but where they have an easy exit so as to avoid making them feel “boxed in”. **Do not actively attempt to create opportunities for the two of you to “bump into” each other; this is creepy and manipulative behavior. Take advantage of the opportunities as they present themselves.** When asking someone out, do not use the word “date”, but also do not be vague about your intentions.

* When deciding whether or not to ask somebody out, ask yourself if you are their equal in most aspects of life. Are they conventionally attractive? If so, then someone asking them out should be conventionally attractive as well. Are they in good physical health (i.e. slim, eat right, physically active)? You should hold yourself to the same standards that they hold themselves in that regard, or at least close to it. Are they career-oriented? They won’t be interested in someone who isn’t at least *working* towards upward mobility, *and* has realistic prospects for attaining it. You don’t have to match or exceed them in *everything*, but you should at least be their match in most facets of life.

* However, in order to date pretty much *anyone*, you need to fulfill a base-level standard. You need to be emotionally mature, responsible, and self-sufficient on a consistent basis in most every aspect of daily life. You need to maintain good hygiene and grooming habits, you need to dress well, and you need to be objectively presentable (even if you’re not conventionally handsome). Your living space also needs to be consistently neat and tidy—no piles of dishes, no dirty laundry overflowing in your hamper, no leaving things strewn about wherever you please, no stuffiness or stale odors, etc. You need to be socially adept and emotionally intelligent, recognizing personal boundaries without needing them spelled out to you. For each of these things, the most important word to keep in mind is “consistency”; it is not enough to live up to this standard *some* of the time. You should be living up to them *at least* 90% of the time. There are *some* people who might still date you if you are unemployed and on disability, or if you don’t have a car, but your dating pool will be significantly limited by these deficits, and you need to be realistic about the sort of person who would want to date you.

* Do not ask someone out if you’re unsure about whether or not they’re single. Do not ask them if they are in a relationship, and do not attempt to be coy in order to find out either way. They will bring it up of their own accord.

* ***NEVER*** ask someone out in situations where professionalism is expected. Do not ask someone out at their job, do not ask them out while *you* are at *your* job, do not ask them out if you have *any* kind of business-related relationship whatsoever (e.g. they’re employed at the leasing office for your apartment).

* **Prioritize *their* feelings over your own. Ensuring that the other person feels safe and comfortable in your presence is *more important* than you getting a date.**

Suffice it to say, these rules make it basically impossible for me to go out with anyone. I’m almost 29 and still haven’t had a single actual date with a woman. What should I change about my mindset? Should I just throw caution to the wind and ask somebody out if I find them attractive and want to get to know them better? What are the potential consequences of me asking them out at the wrong time?