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I recently (Dec 2018) tried to enter the UK after traveling there for a week prior to December with no such trouble. This time however, I was trying to stay for 6 months to be with my boyfriend (UK citizen)... (I know bad move) Naturally and quite stupidly I quit my part time job as I thought I should to go on such the journey. I did not have any money for this trip as I would be relying on my boyfriend to "support" me during my stay there. I did not see any issue in doing this just as long as he could prove his source of income.

With this, I opted for the 6 month instead of say 2 weeks or 2 months (like I should have), i.e. I wanted to spend the most time with him that was possible, then go home. Anyways I was denied entry and sent home due to 'insufficient funds'; e.g. I quit my job in order to come on this trip, so to them I looked as if I cut all ties with my country, when in reality I was just trying to spend some much needed time with my boyfriend.

Long story short, if I try to reenter for two weeks, will I be denied again, being as from the nature of my second visit I was deemed a 'non genuine visitor"? I was told I was better-off applying for a visa. I was just genuinely confused about the rules on going for 6 months as you do not need a visa to visit up to 6 months if you are from the USA. I just want to make sure once I decide to travel again I won't have any hiccups.

Plumdiggy
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It is often a good idea to apply for a visa if you've been refused entry (however, there's no guarantee the visa will be approved, and the 87-pound fee is nonrefundable)

However, you definitely can get in without a visa as well, if first getting yourself a new job (you should do this in advance even if applying for a visa. I'll stress this - hold off your visit until securing a job) and preparing all documentation proving ties to the US and that you won't overstay, work, claim public funds or make the UK your de facto home.

Please upload your refusal letter on here (with your personal details blacked out) so we know exactly what they got you on.

In general, though, you should at least bring any applicable documentation listed here (in "WHAT WE DID") and here (in "DOCUMENTS I CARRIED ALONG"), including but absolutely not limited to bank statements, a return flight confirmation and all relevant phone numbers (and make sure those people are available at any time)

Then be prepared for secondary inspection, and, most importantly, answer any and all questions confidently and truthfully (even personal and invasive ones), not least about whether you've had any past immigration issues (at passport control the officer will see a stop flag, which they will check, but they cannot see at first what it's about)

Additionally, you should shorten down your visit to max 1 month, and spend no more than 3 months in a year (not an actual rule, but my advice based on my own gut feeling), given that you lack a full-time job.

Finally, especially if your boyfriend has stronger ties to the UK than you do to the US, you should consider for him to visit you in the US instead, if at all possible.

Crazydre
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    @Plum they don't normally ask how much money you have on you unless something about you looks fishy to them. Most people from visa-exempt countries who are staying for a matter of months would not bring their entire budget for the trip in cash anyway; they would rely on bank cards. – phoog Jan 08 '19 at 17:53
  • I am also wondering, if I was refused entry- would I have acquired a stop flag on my passport? – Plumdiggy Jan 08 '19 at 17:54
  • @phoog Yes you are correct. I think I got drilled so hard because I asked to stay the maximum length of time with little to no savings (I know it was a very stupid thing to do) Should I inquire about entry clearance?...I have not been suspended or anything, just denied entry. – Plumdiggy Jan 08 '19 at 17:57
  • @Plum if you apply for a visa for a short trip, you can show that you have improved your understanding of the UK immigration system and that you are making an open effort in good faith to comply with it. That's seems to be your best hope here, and it seems to be the basis for the advice in this answer, which seems quite sensible. You can try show your good faith at the border, as some here have done successfully, but the reduced stress of a visa application before you buy your ticket, rather than an entry application after using half of your ticket, probably justifies the £87 visa fee. – phoog Jan 08 '19 at 18:05
  • @phoog Its a small price for peace of mind, quite honestly. I just wish I did more ample research ahead of time to save myself the stress. Thanks for the advice. Last question: If I am granted a visa, even with my history of a past refusal, can I still be denied entry? Or Will my odds have lessened? – Plumdiggy Jan 08 '19 at 18:13
  • @Plumdiggy Having the entry clearance is about as close as you can get to guaranteeing entry into the UK, providing your personal circumstances have not changed and you still qualify for it as you did when you applied for it. The first time you travel to the UK with the entry clearance in your passport, you should expect a short delay at immigration, but to be landed, and to have no further delays on future visits (if you do experience such delays on subsequent visits after having obtained an entry clearance, see this). – Michael Hampton Jan 10 '19 at 03:11
  • @phoog "That's seems to be your best hope here, and it seems to be the basis for the advice in this answer". Not really, I'm basically saying both methods are doable, with a visa however often being safer. – Crazydre Jan 10 '19 at 14:54
  • @Crazydre but underlying both methods is the premise that planning a short trip and showing understanding of the law and a good faith effort to comply offers the best hope of success, no? That's what I meant by "best hope," not that getting a visa is better than not getting one or vice versa. – phoog Jan 11 '19 at 18:45
  • @phoog Ah, then we're on the same page – Crazydre Jan 12 '19 at 11:28
  • Hi guys, thanks for the advice. I am not going to apply for at least 6 months, I think this is my best bet for getting entry clearance. It shows that a substantial amount of time has passed, I have out thought into the mistakes I have made and I am wanting to operate under their rules. It also shows that I have enough funds to support myself (even if it is from a sucky part-time job) especially if I am only applying to go for 2 weeks at a time. – Plumdiggy Jan 15 '19 at 17:46
  • @phoog and BTW, when I am applying for a visa I would apply for a visitor visa (standard visa) right?? I am aware it can go up to 6 months at a time but when it asks the length of stay I am going for, do I put the amount the visa allows for or the amount I plan on going for which is 1 or 2 weeks at a time? Thanks so much! : ) – Plumdiggy Jan 15 '19 at 17:51
  • @Plumdiggy for the length of stay, you should put the length of time you actually intend to stay. Your visa may be issued for six months nonetheless, but if it is, you should keep your trip to the requested length and then plan a second trip some time later. We've had questions here from people who've been found to have used deception for saying one thing and doing another. Given your history, it's best to be clear and consistent. – phoog Jan 15 '19 at 18:04
  • @Plumdiggy Also, if you get a visa, only get it once; no need to keep getting them for the rest of your life, contrary to what some would say. After it expires, you can still enter visa-free and won't face any issues if not making the same mistakes you did the first time – Crazydre Jan 15 '19 at 18:32