Traveling to Amsterdam while unemployed

When I was pulled into secondary the first time, it was due to the fact that I didn't have my return flight information on me, and as I had sort of uncertain answers regarding the reason I was there -- primarily as I wasn't sure what I was going to do while I was there. I was there to meet someone, and was incredibly nervous and unsure if I was actually going to go through with it.. My nervousness was very apparent, and resulted in them pulling me in. It was my first international trip ever, and I was completely unprepared and terrified. My fear basically just made things a lot worse.

Once I got into secondary, the officer that was interviewing me was completely shocked that I didn't carry something that would verify my employment, or a copy of my bank statement. It was only after an hour of so of questioning, and several hours of sitting alone in a small room, did she stamp my passport. It wasn't a pleasant time to say the least.

All in all, my passport got stamped and I was let in.

The reason that they know that I get more vacation time than most Americans is simply as I tend to travel back and forth to the same place a lot now, being that the man I met there the first time has become very important to me. I always say that I'm just traveling to see a friend, but I still get a bit of additional questioning. So, when I go through and they see that I was just there 3 or 4 months ago for a few weeks, it prompts questions of "how can you get so much time off?", which is usually followed by, "how can you afford to come here again so soon?"..

As I'll be meeting him in a different place this time, I'm not sure if I'll have the same issues. With any luck, Amsterdam immigration officers will look at me, look at my passport and return travel information, and stamp my passport. But I can't help but worry as I've never not been asked for additional information.

I suspect what's going on is that they are suspecting you have a relationship, and will either marry and apply for a visa or simply overstay. That's why they want to see proof you;re going back. If you are always flying into the UK, they can of course see how often you;ve entered.

if you read the first chapter of this book you will encounter a similar situation:
http://www.amazon.com/Committed-Skeptic-Makes-Peace-Marriage/dp/0143145754/ref=pd_sim_b_2

Yeah, I think that the issue is that they're thinking I'm planning to stay. In all actuality, I'm just visiting my boyfriend for a few weeks at a time, with no plans of moving there (beyond admitting that it's a possibility to try obtaining a proper fiance visa in the extremely far off future).

The immigration officer I spoke with the last time I went to the UK simply advised me to continue having copies of bank statements, a return ticket, and a letter from my employer. He didn't see any reason why I would be denied entry in the future, so long as I have all that, but he did seem to think that if I didn't have that information I'd get sent right back home.

So...better safe than sorry.

This is why we told you you were over-reacting. You didn't explain the full situation. It also explains your worry about your unemployed boyfriend. So in your case, what you're doing makes absolute sense but it does not apply to 99.9 % of visitors. And none of i will probably happen when entering Amsterdam as you don't have a history there.

So it just shows that the more information provided in the OP, the better the quality of the responses will be. Anyway, it seems you're all covered. have a great trip!