Pressing Automotive Issues

Well, not so pressing right now. A little while ago, though . . .

We've had a weird problem with our Volkswagen Jetta since almost forever. Unfortunately (or maybe fortunately), we haven't had it consistently, so we've never been able to solve it. Sometimes when it's very, very cold, we'll start the car--which has automatic transmission--and then we can't get it out of park and into gear. It's not as locked as if we try to get it out of gear without holding down the break--there's a bit more play--but it's the same sensation. Sometimes it freezes for only a minute or two, but sometimes it lasts longer. I want to say that the longest has been about 12 minutes; I don't think I've ever had to wait a full 15. However, when you're just sitting there in the cold, it sure seems like a lot longer.

We've tried to take the car in to be checked, but the transmission has never frozen when someone is right there to try to diagnose the problem. Lately, though, it's gotten a bit more annoying. If I'm coming home from work, shuddering with concern that I'm going to have to sit in the car while it decides to get into gear, it'll shift right in with no problem. But, if I need to stop somewhere on the way home--the grocery store, say--it'll freeze up when I get back in the car. Although it may not have had time to warm up completely, it certainly should be warmer after having run for a few minutes and then sat for a few minutes than it is after sitting all day. My experience tonight was even more annoying. The transmission hesitated for a second or two but went into gear OK, but then I had to stop for gas. I drove for about five minutes and then pulled into a gas station. It's in around 0 degrees outside, so I certainly didn't linger at the gas station. Maybe it took five minutes to fill the tank. But when I was back in the car, it took six or seven minutes to get it out of park.

We've got no idea of what might be going on. Does this sound familiar to anyone? Any ideas at all?