Is visiting the US difficult for a UK citizen?

My partner is finally coming to visit me here in a few months, but I'm incredibly worried. Despite my poor experience with UK immigration before (where I was asked for a lot of documents that I didn't have -- yet still somehow managed to get in), he doesn't feel that he has any need to carry anything other than a copy of his flight information, and maybe a copy of his hotel booking. I'm trying best I can to get him to ask his boss for a letter saying he has to return to the UK, but his response is "baby, I've been to the US many different times. I don't need that stuff." ... his last visit was about 10 years ago, however.

So... he'll be visiting me using the visa waiver program, staying for 2 weeks, on a brand new passport, most likely carrying only a copy of his flight information.

Is it likely that he'll have problems?

Also, those of you that are UK citizens, or have had a UK citizen visit you in the US before, what sort of questions did the IO ask? Was it difficult? I've heard foreign citizens describe visiting the US as being the worst thing in the world due to the IO officers, so I'm a little scared. (Then again, I've heard people describe UK immigration as being hard to get through, and I only had issues on my first visit).

I wouldn't think he'd have many issues, but unfortunately the experience in immigration largely depends on where he's flying into and the mood of the IO.

My husband (boyfriend at the time) flew into DFW twice last year, once with his mother,  and had no issues. The main questions were, "why are you here?" and, "where are you staying?" but he seemed to receive more of a grilling about the government work visa in his passport.  

I'm glad to see you're getting your fella out there finally!

ETA: I think one of the times (or both, not sure) my husband brought an email printout from his HR department at work stating when he was due back from leave. He was never asked for any such proof, however.

ETA: I think one of the times (or both, not sure) my husband brought an email printout from his HR department at work stating when he was due back from leave. He was never asked for any such proof, however.

I think the proof of work is one of those things that's nice to have, but not always (or even usually) requested. I had an IO advise me to bring it with me on each of trips to the UK, after the first one... and no one has even wanted to see it. I would feel a lot more confident if he'd carry it with him, but men can be so stubborn.

I'm British, flown the the US many times and not had any issues. When I was visiting my now wife I was asked where we met etc, he asked what I did for a living and if I would be looking for work whilst there (which I replied "no" to), they were fine with seeing my return flight details.

Oh, one difference from 10 years, it's no longer a case of filling in the visa waiver on the plane, he'll need to do the ESTA online in advance and pay $14. They recommend doing it at least 72 hours before the flight but I did it last time less than 24 hours before and it was fine.

I'm British, flown the the US many times and not had any issues. When I was visiting my now wife I was asked where we met etc, he asked what I did for a living and if I would be looking for work whilst there (which I replied "no" to), they were fine with seeing my return flight details.

Oh, one difference from 10 years, it's no longer a case of filling in the visa waiver on the plane, he'll need to do the ESTA online in advance and pay $14. They recommend doing it at least 72 hours before the flight but I did it last time less than 24 hours before and it was fine.

Thanks for the reminder at that!
Is he able to do it earlier than 72 hours? For instance, is it possible for him to do it a few months before his flight?

You do it no more than 90 days before travel.

Hi
As the UKC I travelled to the US 7 times over a period of 4 years. This was for 2 weeks at a time. I am generally a worrier and so took with me a letter from my employer and always copies of my return flight. I have to say I was never asked for them. I was asked questions around what work I did, who was I visiting etc.  My first visit I was asked where was I staying, who was I visiting, had I met them before/where did I meet them (I met him online and was honest about this... the IO just said 'good luck'...). It was nothing very heavy though and for me the worst bit was the worry and stress before hand! When I went out there to get married I had everything but the kitchen sink and worried like mad but it was fine.

I have been questioned at Minneapolis St Paul, Chicago, JFK, Newark and Philadelphia and my worry was always worse than the actual questioning.

It sounds like your chap is not a worrier which is probably a good thing and I am sure he will be just fine, especially for 2 week visit. I felt a little less worried with my letter from employer even though I was never asked. I'm sure your chap will be fine but I know it's a worry especially, if like me, you worry. My husband came over here twice for 4 months at a time and each time I worried he would be questioned heavily and they wouldn't let him in. He was not worried at all however...  

Try to relax (easier said that done) maybe persuade him to bring an employers letter saying he is on holiday and will return x date (more for your peace of mind than his though!) and start to get excited for his visit

I would do the ESTA as soon as as. If for some reason he is denied an he will need enough time to go to the US embassy and see if he cant get a visitor visa. He can do it before he books his flights as you can go back into the record and update it.

Thanks for the reminder at that!
Is he able to do it earlier than 72 hours? For instance, is it possible for him to do it a few months before his flight?

Yes it is, it is valid for 2 years.

I would do the ESTA as soon as as. If for some reason he is denied an he will need enough time to go to the US embassy and see if he cant get a visitor visa. He can do it before he books his flights as you can go back into the record and update it.

It lasts for 2 years, so I don't really see the need for flight details on it, or for that matter where you are staying as it's incorrect for future trips....I've never updated info on it after the first use.