Re-making an old friend

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Reiper

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So I have a bit of a dilemma / question, and I am too cowardly to ask someone in real life
(even my parents since they wouldn't understand)

So to preface, I will say that I have never been great at making friends. Throughout various points in my life, I have never had more than a few friends at a time, and I have not had a consistent group of friends all my life. Over time, the quality of my friends seems to have deteriorated. My best friends were probably in early-mid grade school. Some of them moved away, and I moved apart from some of them. My high school friends weren't great, and I have drifted from them, and now I have fairly few friends.

So jumping to present day, I am home from college for the summer, and I have run into one of my friends from public school who lives on my street a couple of times. Usually I am running, so I just say hello or wave (it has been about ten years since we were good friends). The problem is, I cannot get them out of my mind. I feel as though I failed in some way and that I should never have allowed our friendship to drift. Perhaps it is just a mild depression from thinking about what an alternate timeline would look like if we had remained friends or my loneliness from being relatively friendless.

It gets more complicated too. She is a girl, and a rather attractive one, and although I hope to re-initiate friendship I am unsure how to do it. For one thing, even though we were once good friends, it seems there are no opportunities to initiate any kind of dialogue that could even lead to friendship. I see her only occasionally, it is spontaneous and I am running (it would look weird if I just stopped to talk to her).

There is one opportunity in the foreseeable future. A street BBQ that I know she will attend. This is a social event, so it might make contact easier, but it could become intimidating, especially if she is with anyone (family / other friends).

So does anyone have any advice? I suspect many will say what my parents will say "let it go", but I am finding that an increasingly difficult proposition. What can I do / say to maximize my odds of making friendship in this situation? How can I approach her, at the BBQ or otherwise, without it seeming awkward? And lastly, if I do manage to make it through a conversation, how do I ensure we end up meeting / talking again, without it seeming like I am trying to date her?
 

Reiper

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bump, because thread is relevant to my interests...sorry about long read, though I appreciate taking the time to read it
 

Kae

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Well I can't count my friends with 1 finger so I wouldn't take myself too seriously, but why not just talk to her about when you were friends?
That seems perfectly reasonable common ground, or just tell her that you would like to catch up, since you already have some history I don't think you need such a thing as a social event to approach her, but anyway that seems fairly reasonable to me.
 

Dectomax

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Simple really, just stop and talk to her? Take a swig of water and say hello; ask her if she wants to go get a Tea/Coffee/Drink to catch up, or mention your having a BBQ and invite her and a few others over?
 

Goofguy

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Champthrax said:
(it would look weird if I just stopped to talk to her).
No, no it wouldn't. If you two were good friends at some point then it's actually weird that you're not stopping to talk to her. You can't very well expect her to start running with you in order to initiate a conversation. The ball is very much in your court.

Plus since you're running, it would be socially acceptable to not talk for a long time. Just stop, say hi, ask how she's doing, say that it's good to see her, ask her if she wants to play some catch-up over coffee or a drink, exchange contact information and be along your merry way.

If your friendship didn't end on a sour note, then there should really be no reason she wouldn't be open to an hour's worth of hanging out and talking.