Can you send multiple pictures at the same time to someone on the iPhone 4?

If so how?

No. Unless there's an app for it.

Yes. In the text, click the camera icon on the left. Select a picture to send. Click the camera icon again. And then the next picture. And repeat until you have all pictures to want to send. Then click send!

It depends on their data plan. You can send them by going to your photos and clicking the arrow on the top right and tapping the photos then click share the click message. You can only send up to 5 photos I believe.

Ok so click on the photo app then click on camera roll or all photos then in the menu where you see lots on tiny pictures click the bottom left the click on the picture you want and each photo should have a check with a red bubble then on the bottom left click share then click mms or email and there you go hope this helps