I know, I must come off as a particularly hapless case, but I’m not at all used to social interactions. Quite a few months ago I started with Mindfulness training and becoming more aware of my surroundings, at the same time I tried… forcing a smile on my lips in most interactions as I’m noting that my usual empty default expression might add to my off-putting appearance (and realized, oddly enough, how many other people are actually smiling during social interactions and that nobody on the street reacted with dubious frowns towards me, as I had feared beforehand).

The thing is, one of my long-term goals was being able to have a conversation with a stranger… which… at this point seems quite far long in the distance, but I’m still hoping it will be possible for me. In any case, quite some time ago I thought a “natural” situation had maybe possibly presented itself. My usual path to the train station was blocked by a construction site and so I had to walk a long detour for a few weeks. During those weeks there was a woman about my age who almost every day crossed my path, coming when I was going and going when I was coming and after a while I became very aware of it. She also occasionally smiled back at me when I gave her that practiced smile and nodded to her (though more often than not not looking at me, admittedly). At some point I wondered whether I should speak up say something along the lines of “Funny to run into each other so often!”, but eventually was too scared that it might be inappropriate or at least awkward as a guy to say something like this on the middle of the sidewalk to a female stranger.

Eventually the construction site was finished and using my usual route I barely saw her again, now only in very rare chance encounters in town. It still vexed me whether I was a coward or not and so I asked a female online acquaintance about whether I did the right thing and she adamantly insisted that it was correct and that it would have been super creepy if I had said that. Honestly, not very happy with that reply, but I guess it’s plausible. Therefore I thought to myself and ask into this crowd here: Was there any appropriate way to make such a comment? Or was I correct in not daring to speak up.

3 comments
  1. It’s quite common for me on a bicycle commute routine to cross paths with the same person near the same place and same time of day. This happens a lot with many different people. I take many things literally, so I’m not thinking of that situation as “funny”. Plus going to work sucks in general. I’d prolly just say or wave hi, esp if traveling in opposite directions. maybe say their name if we know eachother.

    think of what you’d appreciate from a stranger who you’re not immediately attracted to? Before phones with big screens and internet became a thing, it was quite common for me to ask stories from all sorts of people while waiting for the bus. Open ended question like from some kid wanting a story before bed. what did I get?

    “do you read the bible?”
    Me: “no”
    them: [interesting story about two fallen angels]

    house on chicken feet story

    “at 12:30 in the morning?” [became casual conversation w/ me]

    “um ok, one time at this sex shop I was working at…”

    “once upon a time this guy was pissed off and cold while waiting for the bus and then this kid came up to me asking for a story and I just wanted them to go away…”

    “I have to think about taxes rn, sorry”

    “no, do you?” [became a compilation of life anecdotes]

    alternate perspective of Jack and the Beanstalk

    “ya, I live on the street and it sucks” [had a tone where I thought to just walk away]

    “I’m going to Vegas in four days” [convo was extend to maybe four more lines]

    “ya, I do. I’m a recovering heroin addict.” [said with a tone where I thought to continue convo. wasn’t a bad convo]

    I could note since I asked this to many sorts of men of various ages, like I would’ve guessed same gender as me, with positive responses, I felt comfortable asking who I guessed were women near my age the same questions. and many times they were the ones trying to keep a convo going. now, idk if someone would call police/security with such soliciting, esp now that I’m older and this is the PNW.

  2. You were correct not to speak up. I would have been creeped out. It’s common for strangers on similar routes to give each other small acknowledgments as they pass, “Morning!” etc. It’s not expected to go beyond that, so there was no “chance” that you missed.

    I think most women just want to go about their day unbothered. It’s not complimentary or romantic to be approached by a “same route stranger.” If you had done so, she would have been tasked with rearranging her regular route to avoid seeing you in the future.

  3. I don’t understand the connection between being mindful and smiling.

    But yeah, better not to talk with most strangers.

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