Answering these specifically with Millicanon in mind, so ... possibly a few differences to canon. *grin*
April.
1. Who is your character's confidant?
It depends. Sometimes it's Hobbie Klivian, because you should be able to tell your wingmate anything. Back in canon, it's occasionally Wedge Antilles (pretty much for the same reason, though Wedge has never been his wingmate in the technical definition). And sometimes, in the bar, it's either Atton Rand (Force knows why) if he wants to talk to a guy, or Aeryn Sun if he actually wants anything resembling a useful response.
2. Is your character married? Does he have a lover, significant other, girlfriend, boyfriend?
Not married and never will be, but currently -- well, Hobbie's his best friend, wingmate, and everything, which sort of translates to boyfriend, but he never says that. It's just wingmate. (They build forts and eat Oreos.) He did have a brief relationship with Inyri Forge last summer (who he did call 'girlfriend', eventually), and that's still all a bit messy, but they've both (mostly) gotten over it.
3. Whom does your character live with?
Well ... he lives on-base back on Coruscant, so, with Rogue Squadron, which has been so since he was, um, twenty. (He's thirty and has his own room now.) In about five years, he canonically shares an apartment with Hobbie (I'm not making this up, yo), but I'm not sure when they move out of base. When he's in the bar, he shares a room with Hobbie.
4. If you were to use the speed dial function on your character's telephone, who would answer?
Hobbie. (Guess the theme for most of these answers!) Or Wedge, or Tycho.
5. How does your character feel about his co-workers? What are they like?
His co-workers are Rogue Squadron, who are also what he considers his family. That pretty much sums that up. (As for what they're like, they're cocky fighter pilots. *grin*)
6. To whom did your character give birthday presents last year, and what did he give them?
Well. Lifeday, in the GFFA. And, I suppose, everyone in the squad, though most of those would've been something along the lines of contributing to a bigger thing, or buying them a drink, or something. For specific presents ... probably Hobbie, Wedge, Tycho, maybe Luke, and depending on the dates, Cheriss ke Hanadi. Oh, also, Jaina and Jacen Solo -- it was their fourth birthday, and he and Hobbie (and other pilots?) got Jaina a stuffed bantha, and Jacen ... uh. Something similar. In-bar, um, he doesn't know anyone's lifeday, but he did give people Christmas presents: Wedge, Jaina Solo, Atton Rand, Samantha Largeman, Valentine Wiggin, Brian (don't remember last name, but from Good Omens)...
7. What did your character receive for his last birthday?
Probably drinks from all his squadmates (yay drunk!Wes), and ... probably not anything tangible, really. But something from Hobbie, Wedge and Tycho. But he's not had one in-bar, uh, mostly because the GFFA dating system's a bit weird.
8. What is your character's favorite holiday?
Shadow Night Festival. Which is pretty much Halloween, and he quite liked that in-bar, though he also loved April Fool's Day. :D!
9. What is your character's least favorite holiday?
He doesn't have one, though depending on his overall mood at the time, he can get a bit emo on Endor Day, or the anniversary of the Battle of Yavin.
10. How close is your character to his friends? How well do they know him?
To Hobbie, he is-- there is not a word for how close they are. To be cliche, Hobbie probably knows Wes better than Wes knows himself. He is almost as close to Wedge, and then almost again to Tycho. Inyri knows him pretty well too, after their relationship. And Plourr knows him more than he likes, though he doesn't mind too much, mostly because if he minded, she'd hit him. *grin* In-bar ... his closest friends are probably Atton, Aeryn, Val ... maybe Biggs and Mark ... and again, Jaina knows him probably more than he likes.
11. What is your character's darkest secret? Who else knows about it?
His first kill flying for the Rebel Alliance was a Tierfon Yellow Aces squadmate, Kissek Doran. That's canon. Wedge knows, probably Hobbie knows, and Kell Tainer does because, let's pile on the angst, it was his father. I don't remember if Kell told anyone else in canon (and don't think he has in-bar), but Wes hasn't, whether canon or Millicanon. (This is one of the few things Inyri doesn't know.)
12. Does your character have any siblings? What sort of relationship does he have with them?
Since there's no canon, and not even consistent fanon, this is entirely Millicanon -- he has a younger sister, about five years younger. But, as with the rest of his family, he's not really seen her since he joined the Alliance (just shy of 17). He was a stereotypical protective older brother before that, though, and ... I think this might be why teenage girls have so much luck getting their own way around him. Surrogate little sisters.
13. What is your character's favorite hangout?
Milliways. The pilots' lounge when he's home, but besides that, he doesn't have a regular favourite place in the GFFA, and he really likes that bar at the end of the universe...
14. Where does your character feel most safe?
If he was asked, he'd probably say, "Milliways, except when there's, y'know, crazy bad witches about." But honestly, probably in the cockpit of an X-wing, because even if he's in the middle of a battle -- he knows exactly what he's doing at those controls, he knows who's on his wing, who's got his six, and he knows what he's got to do: shoot at the enemy.
15. Is your character a "regular" anywhere? What do the other people there think of him?
Well ... Milliways. And I guess it depends, but most people either don't know him (at least well), or think he's all right and fun, if a bit silly. I don't think anyone dislikes him, except Montparnasse (who isn't there anymore) and Jack Driscoll (who doesn't know his name). *grin*
16. If your character went to a zoo and didn't have time to see everything, which animals would he look at?
Anything resembling an Ewok.
17. When your character goes shopping, which stores does he frequent?
Toy stores! No, for real, yo. Where d'you think he got Kettch, huh?
18. What is your character's financial situation? How does he feel about it?
Ahaha starfighter pilot pay ... is probably quite a bit, actually, since they either, y'know, die, or retire fairly young. (Wes canonically retires just after 40, which sucks, but I guess there might be IC justification if you look hard for it. *fannish muttering*)
19. What hobbies did your character have once, but has since given up on?
Hunting, and possibly fishing. He didn't live on a farm (not a farmboy, yo!), but definitely very close to one (like, in a village or something), and would have been friends with any farmers' kids. Which doesn't specifically have a whole lot to do with hunting, BUT IT MIGHT.
20. Has your character ever been fired from a job? If so, why?
Well ... he was barely 17 when he joined the Alliance, so I think the only jobs he would've had would be helping out on nearby farms. They probably threatened to fire him for joking around too much, but never did.
21. Has your character ever quit a job? If so, why?
Whatever farming job he had, to go join the Rebels, yo.
22. Does your character have any children? What kind of relationship does he have with them?
THIS IS A SCARY SCARY THOUGHT. No, he doesn't, and he never will (unless previous one-night-stands have resulted in any but ohgods let's not think about that too much). But he has a lot of adopted little sisters (or something) in-bar, and he has it in his head to look after Ben Skywalker if he ever needs it (since Luke's never in-bar), but thankfully he doesn't, because Val would do so first.