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so I am very very shy and making new friends is one of the hardest things in the world for me.

That being said, there is a kid in DS class that he really likes and has asked to have a playdate with. I see his mom sometimes at dropoff/pickup and we've waved/smiled etc. but no real convo. I was working on getting up the nerve to suggest a playdate but couldn't figure out a way to have it organically come up. So that last time DS asked was the weekend before April break. So I emailed the other mom inviting her to bring her son over to play...never got a response

I saw her for the first time yesterday since sending the email and she didn't say anything. Now I feel like a big awkward weirdo and I don't know if I should bring it up.

My DS really likes her kid (it's mutual from what I see volunteering in class) and I don't want my social ineptitude to hamper him. And Other Kid's mom once told me that her son talks about my son all the time, which is why I thought of a playdate.

All that said, I feel like I'm overthinking this whole thing and the solution would be clear to someone more outgoing. Should I say something to her? Any guidance or 2x4s are welcome

Maybe she didn't respond because she's not one to check emails often or got sidetracked. Maybe it landed in her junk folder. There could be a ton of reasons.

If you want to try again you could slip a note into your son's backpack for the teacher to put in his friend's backpack (That's the way it always worked for us in the younger grades in our schools). You could just put a simple note and say "We're going to be at XYZ Park (neutral location so no one feels they have to entertain) on X day and would love to have you join us if you're available. Here is my contact information. Hope to see you soon."

That's just some of the things I've done.

I'm actually emailing a mother of one of DS10's friend and trying to get them together. It gets a bit tricky when they are older and trying to work around activity schedules.

Good luck.

If you've never emailed her before, it could have very easily gone to her junk folder. I'd approach her or do the note thing simplydevastated suggested.

I personally would assume she didn't get the email. AS I know just about anything from an outside source on my workemail gets filtered out through the firewall.

I would get her phone number and give her a call. Say I'm LLL and my son and your son have a lot of fun together at school would it be possible to have him come over for an afternoon?

Don't assume that social awkwardness has anything to do with her not responding. Just let it roll. Anyway, if she doesn't want to communicate it's her loss.

The note is a good idea.

You never know, this mother could be shy and socially awkward as well. Next time you see her just walk up and say, "DS has been begging me for a playdate with your DS. We would love to have him over sometime or meet at XYZ park. What do you think? (or, When are you available, etc.).

I'm pretty shy and socially awkward as well, but I've gotten a lot better by just taking a deep breath and putting it all out there. She's probably embarrassed that she didn't respond to the email (if she saw it). I wouldn't even mention the email...just try to set up a playdate face to face.

I always send a note with the other child that has my name and phone number and suggesting a playdate. Email is so fickle - she probably did not get it. I think you are overthinking the weirdo part. Try once more - you never know, she might become good friends with you too!

I am a busy gal. I can promise you that more than once I've received an invite for one of the kids in passing that I have forgotten about or not followed up on. I would feel absolutely horrible if I knew the other person was feeling badly about it. I make a habit now if someone suggests something when we are at the bus stop or out and about of saying "I am horribly forgetful.. please feel free to harass me about this because I don't want to forget!".

My guess is she didn't get it or meant to get back to it and forgot. I would just try again.

skip the note and just talk to her...

"hi, my son thinks your kid is awesome and would love to have a playdate, here is my number, if you have time in your schedule and your son is open to, it call me"

every mother wants to hear that another kid thinks their kid is awesome...and it puts it in her hands and it gives her an out....she doesn't have to give you an answer right there...and no awkwardness really because she could always say that their schedule is just too tight if she feels the need to respond...but really depending on the type or person she is she just may not respond at all except to say ok i will get back to you and then doesn't get back to you

These are all good ideas. I wish I had thought of the note idea first...I think now it would be weird since I don't know if she got the email or not.

I guess I will just bite the bullet and do it in person. Thanks for the advice. The sucky thing about being shy and awkward is, you don't like to talk about or acknowledge it so you think you're the ONLY ONE IN THE WORLD who feels like a loser sometimes. Nice to know I'm not alone tho...I think really everyone has moments

LLL, I don't have any advice because I'm the exact same way, particularly around other mothers. I feel like the loser who doesn't fit in.

I know this isn't true, but knowing doesn't stop the feeling for me.

Anyway, I wish you well. Just wanted to know that there are lots of us out there. This mom may even be one herself, you never know.

[This message edited by Want2help at 1:20 PM, May 17th (Saturday)]

I always admire the courage it takes for shy people to approach me or others.

I'm not a mom, but I am shy and introverted. Over the years, I've learned the direct approach works best for me. It's the difference between a few awkward minutes vs. overthinking it for days later.

You already have a smile and wave relationship with her, so it's not like you're a creepy stranger in a long trench coat jumping out of the bushes.

I usually just walk up to people with a smile and a dorky half wave. Tell her you're not sure if she got your email or not, but you reached out to her to schedule a play date. Have an opening line ready, so you don't trip over your words out of nervousness.

Most people are nice and a normal person will respond kindly to you. She may be wanting to approach you, too. Don't over think it.

Think of it as practice approaching people. It gets easier the more you do it.

Do you read Real Simple magazine? There was an awesome article this month about being shy. You should check it out.

I am an extrovert, but still have shy times.

I find the direct approach works for me.

Hi, I am Pentup and I am so shy at times, I would rather swallow my own tongue then have to initiate a conversation. But my kid thinks yours is awesome and ....

Or. I feel like a dork asking but I sent you an email.....

Said with a smile, most people will try hard to make you more comfortable. She maybe shy too.