How do you shop for someone you don't know all that well?

Also – I don’t drive and they live about 90 minutes from me in a rural setting. Most of the places they frequent we don’t have where I live (small, local places or chains we don’t have in my state) so I can’t buy say a gift card for their grocery store because you can only buy them in person.

Something delicious to eat or drink (presuming you know whether he has any conditions that preclude him eating certain things or whether he drinks alcohol). I found this slideshow with ten of the best liqueurs for Christmas. Not something I’d ever buy myself but I’d love from someone else.

Or a box of beautiful, artisan made chocolates. Not your run of the mill stuff. Something special and beautifully boxed.

Food/drink isn’t a bad idea. It may not be the most creative thing, but it’s still something good to fall back on, in case no other ideas seem to work out, since everyone eats and drinks. And because most of us indulge a little bit around the holidays, it would be hard for it not to be appreciated.

When you’re around him, what have you seen him doing most of the time? Spending time outside? Watching TV? It might be helpful to think of something tailored to what you see him do most.

I don’t think you can go wrong with a gift basket of goodies like coffee, candy, cheese and crackers, maybe wine. And be sure include a hand-written note. It will be appreciated and remembered. You might even make a little joke in the note about not knowing him well—hence the variety of goodies.

Something nice but practical – a nice frame, for example. It’s something everyone can use. You can get a nice one for less than $20.

A gift basket of goodies is a good idea BUT it’s going to probably cost you over $35 unless you make it yourself. Even if you make it yourself, it’s going to cost you some bucks.

If he drinks wine, you can get a few bottles of wine, or if he drinks beer, some unusual craft beer can be a fun gift.

I went super lazy this year and rounded up photos that were centimental and had these guys print them up. It is fairly cheap and the quality is a lot better than I expected. If you have a picure he likes it is option. I have a frameless one on my desk that was takeng from a low quality scan and it is actually kinda stunning.

It’s so hard to buy something for someone you don’t know well, and I think it’s worse when it’s a man. Since you are friends with the wife is there no way to being up hobbies your husband has and maybe she will talk about the hobbies her husband is into?

The food gift baskets are a good idea if you really have no idea although they tend to have fattening food, so even that can backfire if he is very health conscious. No matter what he will appreciate the thought I’m sure.

Since he has helped you I assume you have met him in person (although maybe not) so you could consider a t-shirt, polo, or rugby style as a gift. If you live in cold weather a nice pair of gloves and a scarf is another idea.

What has he done for you? Does he work with tools a lot? Does he need new gloves and hat? Does he drink? Does he like music? Movies?

Doesn’t have to be fattening stuff, @JLeslie. @hug_of_war could put together a lovely basket of “safe” foods like fresh and veggies, fruit, etc. and still include a low-sugar cookie or other dessert.

@Pachy I know. Those are usually more work. The OP might be very willing to do the work. The ones that sit on shelves pre-made usually have the less healthy stuff. Depends on the store. I once did a basket of pasta, pasta sauce, oil, biscotti, bread sticks (the Italian packaged kind) I like that sort if them. The low carb people might see it as unhealthy, but nothing in there was particularly bad in my opinion. The woman I have it to is Italian and likes to cook though, so I had some guidance in my guessing.

I also once did apples, caramels, chocolates, pecans and walnuts. Kind of a broken down specialty caramel apple.

Why not get a gift cert. for a local restaurant for the 2 of them?
Depending on what you can afford, maybe $50—$75 which would be more than enough to enjoy a nice meal at a decent place. You could find a unique, out of the way place or just go for something popular like Olive Garden or Strings or a Steakhouse or ethnic place such as Thai or Italian or Greek.

I like cinema gift vouchers too. Is there a cinema chain near them? Most people like watching films and you can get a card for a set amount.

@Earthbound_Misfit Yes, good idea, I just got a $25 movie card as a gift. Yay!

A lot of good answers, I definitely have a lot of ideas floating around now.

I’ve spent my entire adult life plagued by this question, and like all the other great riddles that have plagued us through the ages, I’m still at a loss. And now the annual agonizing over this sort of nonsense is confronting me. I hate it!