help for an overweight friend

So one of my buddies contracted me to help him lose weight, mainly because he knows that when I start something I won't drop it till it's done, but also because he knows I wont make fun of him or anything. His stats are 5'5, 250lbs (about). He (up until now) has lead an extremely sendentary life, like playing World of Warcraft day in day out. So recently, about 2 weeks ago, weve started taking walks and they usually add up to about an hour. We do this daily, and I know that he's been going through some hard times, so he hasn't been eating much. But basically, my question is, when is it a good time to start other exercises, and what should he be doing? Ive searched and searched online, but so far no website has been giving me an answer. I don't want to end up pushing him too hard, I know it would be unhealthy and he would most likely lose interest if he's not having fun. So if you have any tips on how to go about this, let me know! thank you!

walking is a great place to start because it's not intimidating.  you can start introducing some short jogs any time.  a little light weight lifting would be good, too, because he'll see and feel the results very quickly.

i don't know what kind of climate you're in, but shooting hoops or ice skating might be a good idea. 

Lifting light weights (5-10lb) is a nice step up, maybe add some good stretching before your walks, or play frisbee/toss a football.  pgeorgian's idea is great too, a little jog in your walks to spice them up!  (Ice skating is ruff if you've never done it before lol - just make sure you have the pads/gear to work with it).  <3

I think you should keep walking until he starts to see some results and gains a bit of confidence. If he's lost 10 lbs, for example, he might be motivated to try new exercises that will get him and the weight moving.

The thing that will have the greatest impact on your friends weight loss in the shortest time is getting his diet in order.  He needs to figure out how many calories he's burning in a day and how many he's consuming.

I think you've got him on the right track with the walking.   But like floggingsully said, if he want's to lose weight then getting him to count calories, eat heatly, and so on is going to help more than anything.

The sad thing is, he has to want to lose the weight bad enough to actually take control.  You can't manage his calories for him, he actually needs to do this for himself or it'll never hold.

yeah thanks for all the advice... i'm going to try and get him to join, though right now he's still living at home, and well his father doesnt make the best food choices, and presently he is without a job, so it's very hard for him to always eat well. though i have to say he makes an effort at trying to eat the better from the selection he has right now. I'm confident he's tired of being as he is, and that he wants to make a change. Until then, i'm going to get him jogging. And to answer the other question, I live in Quebec Canada, so our weather is... well... everything lol

Probably the biggest thing for me, as far as exercise is concerned, especially when just starting, was doing things I enjoyed.  ie... playing racquetball, wallyball, walking etc.  Activities that got me moving, but didn't necessarily seem like exercise.  Now I enjoy the aerobics, walk/jogging, weights, but I most certainly would not have liked these at first.   

If he's been that sedentary, he won't want to push it too hard just yet - he probably doesn't have the stamina/strength. Just walking is perfectly good exercise and it'll get him into the habit of exercising REGULARLY - you can make the exercise harder once he gets used to it and it gets easier.

Look for the "Couch to 5k in 9 weeks" running program from CoolRunnings.com.  There's a Podcast (google for it) that someone did for it, too.  I started it 1 year ago barely able to run the 90-second intervals.  Now I run 3.1 miles, three times per week.

I'm no longer 235 lbs, though; he will have a hard time getting started.  It's ok to take more than 9 weeks.  It took me about 9 months.

Also -- watch his deficit.  If he adds exercise, make sure he doesn't increase his deficit over 1000.  In other words, he should eat more when he exercises.  This is to avoid starvation mode, lowered metabolism. 

i think jogging is probably too much until the walking becomes very frequent and brisk. I have never been really overweight in my life...yet jogging took me 3 months of going to the gym to accomplish for more than 3 minutes because it is hard to train the blood and oxygen to circulate quickly enough. Someone who weighs much more will have a much harder time, and I can say it is very discouraging if introduced too early (not for me last time i tried, obviously, but for many.)

it might have a reverse effect though if he really likes taking challenges, who knows! But if his mind is on harder things right now like you say it may just slow progress. I know it slowed me when I was battling depression, I quit trying to do anything for an entire year until recently

As a fella, I have to say that you'll hurt his pride the least by getting him into the gym. Bigger guys can squat a lot of weight. It's absurd really.  I'm 6'0" 170lbs and usually do 170 lbs for like 10 reps (very low). Bigger guys adapt quickly because they're used to lifting more weight all the time. Seriously, get in there and have him build some muscle because if he builds 5 lbs and sits all day, it'll burn more calories than running for an hour then pouting about it.