How to start a conversation with someone you don't know?

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There are several possible reasons to argue against such self-perceptions involving your anticipation of failure (which become, through various subconscious mechanisms, self-fulfilling prophecies).

1) The person whom you are aiming to approach is ideally a total stranger, and will most probably stay that way whether your attempted social overture is accepted, or whether it fails, at whatever stage in proceedings, with whatever degree of (self-perceived) seriousness in terms of social malfunctioning, and with whatever degree of embarrassment you consider to be (immediately or after subsequent (typicially lone and socially-undiscussed) consideration) justifiably self-inflictable (this usually resulting -- after ridiculous levels of self-criticism are applied with no external reference points -- a firm intention not to pursue the line of activity in question.

2) They were a stranger and they usually remain a stranger in either a positive or a negative outcome (to whatever degree that 'negative' is objectively verifiable as a relevant outcome, i.e., probably not very unless they become hostile toward you, which isn't likely -- most people are good and positive in outlook).

3) While no-one likes to look foolish in front of anyone, all you're doing is making an opening casual gambit, which could result (but which will not inevitably result) in a conversation which where successful will be typically short and impersonal (but to which they may or may not respond, for various reasons, which would not be a personal failure). So as long as you don't get so nervous that you piss your pants or have some degree of autistic meltdown while attempting to interact, you're doing well.

4) You don't have to expose what you might (justly or otherwise) regard as personal weaknesses to this stranger (who, let us remember, you have already fixed-upon due to various factors that tend to indicate their possible potential for even the most limited sociability -- these will be verifably identifiable in the majority of positive and uplifting situations -- e.g., You are at the seaside, and have perceived an obviously emotionally-elevated mother with happily-excited children in tow (who is, for example, a more likely responsive subject than a morose-looking male who is sitting on a bench and cleaning his nails with a hunting knife,) and who apparently offers far more scope for a spontaneously and personalised approach (perhaps about what fun the kids are obviously having ("wish I were that age again..."), or imparting some relevant personal knowledge and/experience of good spots for the kids to go crab-fishing) and for subsequent but inherently unpredictable potential response).

5) On the other hand, the man cleaning his nails with a knife might be a more receptive target, if you are in a similarly downbeat and cynical mood (as you reasonably adjudge him to be). You might have a specifically-relevant experience (say, the best type of hunting knife for nail cleaning) or -- perceiving him on some grounds to be an Army Vet -- you might be able to approach him on the grounds of civilian sympathy for the plight of the enlisted and then disregarded serviceman. This approach could take time, involving settling down near him, without alarming him or making him suspicious of you, and only trying to initiate conversation after a lengthy pause, to which he might not response at all, or perhaps only after a similarly lengthy pause (see slow-motion inter-male conversations, described above). Or you could approach him with a the potential to take some offered seaside food. Or perhaps he's too forbidding to approach at all. In which case move back to the exuberant mother, or to some other individual (perhaps as yet unidentified).

6) If you are thoroughly-rebuffed by any and all of your potential targets, failing to even strike up a basic conversation, consisting of your specific approach and a non-committal answer from any of them (and this is overwhelmingly unlikely as an outcome for all but the most comprehensively socially-inept, inappropriately-behaved and/or physically intimidating subjects, because people overwhelmingly tend to be socially-spontaneous when they're happy (which should mark them out as likely targets for your attempted charms), and they often strike up temporary relationships with an apparently trustworthy stranger (ie., you) who is subsequently adopted by the individual or group, and is as a bare social minimum not expected to say anything negative, but to go along quietly with any individual or group or crowd of which he unintentionally finds himself a part (this is a tendency that has often got me into some unexpected places and situations, even here in supposedly emotionally-repressed Britain. including entry into illegal underground cannabis clubs (which always frustratingly elude subsequent detection in the cold and sober light of day even though you know you signed the register and were therefore accepted as trustworthy), onto nightclub doormen's guestlists (through God-alone-knows-what string-puling), and into strictly private and often sexually-diverse or indeed perverse environments), and if so then perhaps your social outcome will not be mere conversation but some spontaneous involvement in some unexpected group activity.

7) Why worry about looking an ass in the first place? NT do this sort of thing all the time. Except where there's a strong degree of sexual attraction on the part of the conversational initiator, and an equally firm rebuff or unwelcome specific reaction by the proposed object of their affections, they are not in the slightest bit embarrassed (athough perhaps unable to comprehend how their considerable person charms did not achieve the desired result) and this frequently does not stop them from making further advances in the hope of 'winning her over', efforts which are frequently met with further derision or blank rejection, and which the make NT tends to regard as part of an ongoing game to overcome her defences and so on -- and the awful thing is, this strategy of attrition sometimes works!

So when you consider the possibility of making an ass of yourself, try to remember that the only person who perceived you as an ass is yourself. The rest of the people who you interact with, or are observed by won't even remember you tomorrow, so why should you remember them and torment yourself with their (real or -- mainly -- imagined) reactions for the rest of your life? Get yourself out of a doomed conversation as soon as you recognise it, by saying a cheery "Enjoy your day" or "Have fun" or "Mind you don't catch your nose in the door" or whatever and then simply walk calmly away from the situation, choose a suitable spot to breathe a little sigh of relief, reflect on what's just happened WITHOUT blaming yourself unnecessarily, collect your wits, gather up your confidence and then turn around, best fake real smile at the ready, and prepare to start again with a new (and promising looking) person.

Your characteristically autistic tendency to paranoia may begin to whisper to you that you are attracting unwanted attention to yourself by onlookers, but (a) this is very unlikely, dependent on the crowdedness of the venue and (b) paranoia is a form of vanity, in which you are somehow the centre of everyone's over-analytic attention.

And if all else fails, remember the lesson of Robert the Bruce: Run away and live in a cave.

Thank you again.

But whatever recreational stimulants you are taking, we need to destroy them

Criticise my navigation and driving skills, not the fuel in the tank.