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A lot of the time (3-5 times a month) when I'm walking in the street or sitting on the public transit random strangers will make eye contact with me for more than 3 seconds and also smile at me in a way as if they want me to talk to them or something. In all of these situations I try to smile back while walking (or while sitting if I'm sitting) and then continue on my way (or look the other way) but sometimes I feel like I want to get to know the random stranger too as they have expressed interest. To clarify, I'm talking about situations where it's more than just a quick glance and smile, but a prolonged one that may include other things too such as turning to face me. What can I do in order to do this successfully without it being awkward or intimidating the other person in the off case that they didn't want me to approach them, and also to befriend the individual in the process if they do?

edit: M/20

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If you are standing close to the person, make a casual statement about the weather, or something about the public transport today, or some other totally benign topic. This gives the person who smiled at you a chance to react.

Be cautious as the person who seemed interested may have just been courteous. If they respond to your statement by grunting or smiling then looking away, then they don't actually want a conversation.

If they seem interested however, ask the person a question about themselves. It gives them another chance to decline the conversation, via giving you a short answer. If they are interested however, this gives them an opening into the conversation and you can take it from there.

Careful not to walk towards someone from a distance based on a small amount of eye contact and a smile however. This can be seen as threatening and intimidating and generally leaves a bad impression.

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  • Thanks I was mainly unsure about your last point but I'll make sure not to do that except for extenuating circumstances as I have wanted to sometimes before. Do you have any recommendations on what to do if it's at a reasonable distance and you're 100% sure of it? (to minimize awkwardness and bad impressions if you're going to do it approach them anyway)
    – LDR
    Commented Aug 3, 2018 at 1:40
  • Make it seem almost accidental. Go over to look at something behind them or around them. But if you are outdoors in a public place, I'd really caution you against doing this. At the very least try to make eye contact again and see if they hold the contact and smile, or if they look away. Slow and steady with lots of chances for the other person to leave is the secret to not be a creep in public.
    – EmandM
    Commented May 20 at 23:33

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