The obvious and empowering and “you go girl!” answer to the question posed in this post’s title is “Of course not.” I know that that’s the right thing to say, and it’s what I’d like to believe. It is definitely the advice I’d give a reader if she asked.
But it’s not always so easy to take our own advice.
Here’s the deal. There’s this girl in Chicago who I run into every now and then at parties, bars or other social gatherings. Whenever we see each other, it’s friend-love all over again. We chat at length, we laugh a lot and we always, always, do that thing where we say “Why don’t we ever hang out? We have to get dinner. Seriously this time, though. Like, for real. This is getting ridiculous. I mean it this time.”
Then a week or so passes and I get caught up in work and life and my existing friends and I forget to email her, and she doesn’t email me, and we don’t end up getting together. I’m confident we were both sincere when we said it, but the moment passes. Nothing happens. And then a few months later we run into each other at another affair and the whole thing happens over again.
I was thinking about her today. I haven’t seen her in a while, and I really would like for us to hang out. I think we could be best friends. (When I say it so bluntly it sounds silly and childish. But whatever, I really do think that.)
The thing is, we’ve been doing this dance for so long that I almost feel as if we’ve missed our window. That, somehow, the bar banter and the “no, really this time” has become our special thing. Basically, I think it might be too late.
Rationally, as I write this, I realize I’ve got the perfect set-up for a pick-up email. I should just send a note that says “I’m finally making good on our promise to get dinner.” That’s what I did throughout 2010, when I was going on one girl-date a week in search of my new BFF. But somehow, even though I knew this girl last year when I was making it my business to ask girls out, I never mustered up the courage to go there with her.
There was a part of me that was intimidated by her back then. And now there’s a part of me that worries what if we meet and it isn’t the easy, hilarious conversation that sprouts up when we organically run into each other? What would happen at the next birthday party of a mutual friend? Would we get awkward?
Since I know I’d tell any reader of this blog to send that email, I’m going to vow–publicly, right here–to email her. This week. I’ll do it, I swear. But has anyone else ever felt like I do in this situation? Ever met anyone great, and done the whole we-should-be-friends dance so often that it starts to feel like the true friendship window has passed?
MWF Seeking BFF 
I know exactly what you mean.
I do think there’s that window… but I always judge a person by intention and I think if your heart is honestly wanting to make a friend, you should do it even if it feels awkward. She won’t think you’re being silly and you will feel better for having taken that action.
Can you tell I’m a coach? 🙂
Definitely go for it…she will probably turn out to be great! I would say the time clock restarts each time you recommit to getting in touch. And she will probably be happy that you were the one to finally make the move.
She probably feels the same way and will welcome your invite. If not, there is no reason to feel awkward in the future since you already know you both have similar humor and mutual friends.
I think it’s a WIN/WIN.
I agree with you and everyone. There does seem to be a window – the question is: is the window actually there or is it a society imposed window that we just can’t seem to get past?
Good luck! I hope the email comes out just like you want it to and you guys can plan to get together (goodness knows that I would write that email ten times over before sending it)!
You should just do it. Sometimes people really DO mean that they want to hang out in the future, and life just gets in the way of reaching out to make plans. She probably feels just as awkward about it and would love to hang out with you. So just go for it.
And if it doesn’t work out, you can still be friendly to each other as mutual friend events.
I have a been the exact same situation…every time we bumped into each other we would fall into an immediate comfort zone, acting so at ease actually the feeling was similiar to…” I feel like I have known you my whole life”…so I decided to just try to jump the relationship to real friendship, issued an invite for drinks that we could never seem to get scheduled….and unfortunately we never seemed to develop the follow through with one another. Thinking about it now, it is really strange…if we casually ran into each other we could talk for hours, but could never really move forward…so I decided to just accept it for what it is…I like her so much, that I love when we do get a chance to talk. So yes I do think that there are certain windows, kinda like if we both think the other is so great why can’t we seem to find the time, even if that is not the case, the under-lying feeling is there.
Maybe this lady and I started to doubt each others intentions….like thinking o’ she says this all the time it means nothing..
I definitely know what you mean with “there is a window”… it seems odd that after such a long time you both haven’t tried to turn this really great chemistry into more than occasional run-ins … but I don’t think it’s too late. She’ll probably be REALLY happy that you made the first move. (Hope you’re going to post about her response :))
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