My toughest paddle out/most memorable, would have to be down in Rodanthe a few years back. There was a huge south swell, with a good 8 mph south to north current. I didn't want to paddle out, but I let my two crazy friends talk me into it. We paddle out just north of the pier and by the time I made it out, I was just passing S Turns (around 2 miles down the beach). The waves were just freight training rights, a couple feet overhead and more rectangles than round, just throwing out thiiiick barrels. I kept missing waves, half because they were impossible, half because I couldn't bring my self to jump over the ledge. Finally I realized that I couldn't see Rodanthe anymore and that I was going to have to make it to shore at some point. I paddle as far in as a I could and caught a medium sized one, and it was by far the fastest wave I've ever caught.
I was so stoked I paddled out for one more and in the process, took the heaviest lip to the head during a duckdive that I saw stars. My head almost got smashed into my board and I was immediately sucked back over the falls upside down and throughly thrashed, but I didn't let go of my board, even though it was way oversized for me/conditions (6'2 Santa Cruz fish, I only weighed in around 145).
Anyways, I finally made it to hwy 12 and started the 5 mile walk back to Rodanthe with my thumb out, trying to hitch a ride. I must have seen 20 empty pickup trucks drive by (fishermen hate surfers I guess) before a chick in a tacoma with only room on the tailgate to sit, gave me a ride back to town. It took me a couple nervous hours to find my other to buddies by driving down HWY 12 and running across the dunes looking for them up and down the beach.
That's intense man. Had a similar experience in RI during pre-hurricane swell. I tend to agree with Lee that the right coast is self-regulating, but everyone has those moments where the force of the ocean shocks them, and one of the craziest for me was during Irene last year. I was watching the path predictions early, so I went into angry broad deterrence mode. I planned a "getaway weekend" with the girl near the beach (that is generally clean during solid E/SE swell) before she heard about the storm and subsequently wanted to spend the weekend watching point break and listening to the rain... I’ve digressed.
The point I was going to make was I believe it was Sunday right at the end of August, and you could tell the hurricane was passing. The barometer was still all screwed up , winds were ~30mph NNW, it still wasn’t friendly out. I was parked on a bluff overlooking a NE facing beachbreak w/ miles of beach north and south. The ocean was still looking a bit discourteous, and after an hour of convincing myself the waves were shaping into a-frames, although uncomfortably large and most likely unmakeable, I considered suiting up. At this point an SUV driven by a once-hot soccer mom pulled up. Immediately two kids, maybe 17, jump out with bodyboards, sprint down the cliff just frothing and jump in. I’m not kidding when I say within one minute, the sideshore had swept them so far north they were gone - couldn't see them from the cliff. Until then I never thought someone was going to literally get taken into the Atlantic. It must have hit the mom all of a sudden because she stopped smiling, then she started losing her sh*t. I told her to follow me to the next beach, about 2 miles north, because there was no way they were making it back there. Some guys used to intentionally drift the beaches, but not like this. She followed me to the next beach and we just watched. After about 20 mins of waiting we were about to make some calls. Finally two black dots came into view on the beach… from the north. They were panicked and said they tried coming as soon as they got in but they had absolutely no control – they went north and then got pulled into a rip and they were fortunate to hang onto their boards and caught some lucky waves which eventually deposited them on the beach...3 miles from where they went in. Hurricanes carry a lot of power. Anyway I'm sure that would have been my worst paddle out had I made it in haha. Sorry for carrying on and a lack of paragraph separation but thanks for the good stories.