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I will join my future husband (Spanish) in the UK, entering on a Standard Visitor visa. (I am Chilean).

Two months after joining him in the UK, we intend to get married in Spain, and return to the UK.

Will I have trouble re-entering the UK as a tourist the second time (now married)?

Can I apply for the EEA family permit from within the UK?

Just for context, I am allowed to stay 6 months vith my tourist visa.

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    I assume you mean you ‘intend’ to get married, not ‘pretend’? Not a mistake you’d want to make if talking to an Immigration Officer! – Traveller Nov 1 '18 at 18:35
  • There's an archaic meaning of "pretend" which means ( merriam-webster.com/dictionary/pretend) "to venture, undertake." Many Spanish speakers fall into this trap since both pretend (that meaning) and intend can be translated as *pretender". Though yes, it would be better to use a different word in conversational English! – Roddy of the Frozen Peas Nov 1 '18 at 22:55
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You cannot apply for an EEA family permit in the UK:

You must be outside the UK to apply for an EEA family permit.

You can enter the UK as a tourist even after you are married, if you are in fact planning to visit for the purpose of tourism. If you plan to remain in the UK under the freedom of movement regulations, you should say as much to the immigration officer when you enter the UK. You do not need an EEA family permit to do this as provided in the Immigration (EEA) Regulations 2016 at regulation 11(4) (emphasis added):

(4) Before an immigration officer refuses admission to the United Kingdom to a person under this regulation because the person does not produce on arrival a document mentioned in paragraph (1) or (2), the immigration officer must provide every reasonable opportunity for the document to be obtained by, or brought to, the person or allow the person to prove by other means that the person is—

(a) an EEA national;

(b) a family member of an EEA national with a right to accompany that EEA national or join that EEA national in the United Kingdom;

...

You will therefore have to prove the validity of your marriage in this case.

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    gov.uk/family-permit – Traveller Nov 1 '18 at 18:38
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    Note that when Britain leaves the EU on 29th March 2019 the existing freedom of movement arrangements may no longer apply. It remains uncertain what arrangements will apply after that date. – user79658 Nov 1 '18 at 19:23

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