What's the most uncomfortable situation you've experienced in the military?

While in Okinawa I met a girl at a night club (of legal age). I got her phone number and went out the following weekend. After having a flirtatious evening she took me home. I seen a pic of her dad and then asked to see an I.D. It was all good. I asked her where her father was and she told me in Korea, but will be home on Monday. She said she wanted to take a shower and I followed her in. After sudsing each other up we hit the bedroom. - Great time I might add.
I passed out and in the morning we got "busy" again. Suddenly I hear "Cough Cough" I turned around and there was her father. A huge man who happened to be another Marine. A Major. Alicia's backside was sunny side up and I did like any other enlisted Marine would do....salute. Oh yes both appendages were saluting. The real bad thing is that we were in his bedroom. '
There was two ways out....the window or face him like a man. I put on my pants and grabbed the rest of my clothes while he stood in the doorway. Alicia just crawled under the covers. His hand was on the doorjamb and I tried ducking under it as he wouldn't move. While holding his hand out for me to shake, he then said, "Oh, a Lance Corporal! I didn't even catch your name son." My reply, "Lance Corporal Friend Sir." Boy was I shaking in my boots. He firmly shook my hand and punched my face with the other. I don't recall ever being his so hard in my life. I was on the floor and he was still holding my hand punching me over and over again. I crawled for the door, made it out and never looked back. This was my awkward moment

While working at HRC-STL (Army Reserve's HRC) my coworker and mentor, a MAJ, was having a discussion by email regarding "women in the military" with a female colleague, a peer of his. He invited me into the conversation by forwarding the email thread and encouraging my input. Having gone from infantry to AG and being decently read on the subject, I weighed in. She did not reply to my comments.

A week later I discovered she disagreed with my rationale so much that, rather than approach me (a CPT), she filed an EO complaint, which I found out from my leadership. The EO officer encouraged me to apologize in writing and she expected a one-on-one. My supervisor insisted on coming but was thrown out of the meeting because they got into it. She was melodramatic about how personally she took my commentary and tried to chew me out and realized my nonapology apology was insincere (I apologized for emailing her my thoughts).

It was quite uncomfortable getting ripped for the audacity of having a difference of opinion on personnel policy by a senior officer who didn't have the backbone to come talk to me professionally about something like this in the first place.

Tailhook.
In the midst of the scandal all the men in the command were brought into the base theater and informed that if we said, or did anything that was offensive to a woman, we were guilty of sexual harassment. Knowing that it would literally be impossible not to say or do anything that someone, somewhere would not find offensive, this was a frightening time. over the years the definition of sexual harassment changed several times to what it is now, but for quite a few years it was quite sketchy.

I was a SP4 (P) driving a jeep for the S-3 in our Combat Engineer Bn. at Ft Meade, MD 1979 - on an FTX and tasked to take a new butterbar on a route recon. Range road had a Bailey Bridge over a river, and the bridge was temporarily out (simulated bomb damage). It had rained enough the night before that the fording site (next to said bridge) was way too deep and fast for my M151A2, even with snorkel installed. Well, my butterbar OIC was not going back to the S-3 TOC with bad news, so he ordered me to proceed through the ford. I told him it was a bad idea, but the "West Point educated" officer was certain we could make it. I informed him it would take a written order from him, and he obliged, saying that "the Colonel would hear about this!"
I swam away from my jeep being washed downstream, and told the LT I would hustle back to the AO and get us a tow.
That night, I was chewed by the LTC S-3 for losing his jeep, until I showed him the water-stained written order in my little green notebook. He actually then broke down in laughter (I had to join in) at this "dumb-ass rookie butterbar" who was responsible. He told me I should try harder to keep these 2LT's from making idiots out of themselves!

Walking through the airport in San Francisco under orders to not respond negatively to people calling me names and spitting at me.

Cpl Justin Goolsby
I have two. Both, unsurprisingly perhaps, related to girls.

The first one was at CTO A school in Pensacola. One evening a young lady and I found a nice, unlocked lobby to..well, you know. So of course an instructor walked in. Hard to say who was more shocked, but quickly turned away and kept on walking. We made a hurried exit.

The second was in Japan. I was at my GF's house, and she and her roommate were arguing badly enough that I thought it was going to come to blows. Well it did. Only I was the one that got hit. See, the roommate, who had just gotten out of the shower and was wrapped in a towel, decided she'd piss off my gf by dropping said towel and laying down on the bed, with the intent of drawing my eyes to her. Being young and stupid, I cheerfully obliged, and didn't turn away. The gf screeched, swung at me, and I still have the scar from that scratch on my chest today!

That's a common occurrence with small children in the military. Daddy wears a uniform. They see a uniform and they think "Daddy". Believe me...when the child's father gets home he will be "Daddy" and that bond will be reestablished. Awkward situation...my then wife was a secretary for a high ranking officer, and got involved in the investigation of the base XO, who saw to it that our tour in Japan was cut short (he had us sent to Miramar in San Diego. Like that was punishment). I had two weeks to check out, and I had to check out with...that XO. I was just a PO2...and we had a stare down...I knew he was wrong...and he wanted to burn me. I told him just initial my sheet, or keep me there and charge me with something and I will request a court martial (as I had done nothing wrong, and I knew he didn't want that given what he was involved with). After arriving at Miramar we learned that commander was busted and kicked out of the Navy.

Being pinched by a SMSgt. He was very handsy, all the young female soldiers tried to avoid being around him, especially alone.

I had left an airborne unit before females were allowed to jump. I was a jumpmaster and there were a couple of females that were pay hurts jumping. I was doing the JMPI and I said squat and hold. I was stomped for a minute and very uncomfortable. In the JMPI you are suppose to run your fingers inside the leg straps to ensure that they are not twisted. Young soldier said do what you got to do jumpmaster! I actually broke out into a sweat.

Going to the funeral of a man that a vehicle in my platoon accidentally collided with on a highway in Iraq. As the platoon leader, I was tasked with representing my command, offer our condolences and distribute $3000 in compensation. I would say that was one of the more uncomfortable experiences in my entire life and I am actually surprised his family didn't kill us.