Hello all,

Im looking for some help on what to tackle first and how to get better with hills.

Just some background first, after 6 months of dieting and 3 days a week of running I got down to (6'2") 170lb from 240. For the past 4 months Ive been maintaining my weight and worked up to doing a ~32 minute 5k (9:30/Mile) Within the past month I purchased my bike and have been slowly ramping up my rides because of typical sit bone pain. Im currently up to 20 miles but will be shortly pushing for more.

In the meantime, Ive been working on my hill climbing when I dont have alot of time to ride. The second ride I took I did a .7 mile @ 6% hill in 4:07 I felt like I was going to pass out at the top. 4-5 rides later after getting up to the 15 mile mark I attempted the same route again, and did that hill twice, I felt much better after getting to the top but found that I ran it in 5:27 and 5:32. I felt pretty bummed after that. I also attempted a .2 mile @ 9% hill a few days beforehand and got my butt handed to me and had to stop halfway up.

Have a couple hills nearby as options to train on.

.5M @ 6%
.9M @ 5%
.2M @ 10%

Im sure after only putting ~60 miles on my bike '15 Allez Sport 50/34 - 12-27 I still have a LONG way to go, but I was just hoping to get tips from you guys as how to start out and how to know when to stop pushing too far "into the red" as they say.

TL, DR - Hills suck, want to get better. I know im a newb.

I think, instead of trying to go up the hill as fast as possible, you should work on slowly increasing the pace at which you can go up the hill without killing yourself. You will never be riding short hills in isolation, they will always be preceded and followed by a lot more riding. So find a pace where you feel comfortable, go up the hill. If you still have gas left (and you should) then go down the hill and do it again. Repeat until exhaustion.

There's no trick to going up hills. That said, the trick to learning how to go up hills is to do it slowing at first. Very slowly. Also, I've learned to think of it like this: you have two different engines for going up hill, your lungs and your legs. You can essentially shift nearly all of the burden to your lungs/cardio system by dropping it into the 34/27 and spinning like mad. You can essentially shift nearly all of the burden to your skeletal/muscular system by dropping only into the 24/21-23, standing up and basically stair-climbing it up to the top. Really, you want a mix of the two, because then neither system gets totally drained. But the only way to master that is by doing a lot of hills.

Problem you have is that your hills are too short. You need to raise your FTP, or functional threshold power. That's best done with longer efforts, such as 2x20 intervals. The short intense hill climbs that you're doing, while helpful, are working more on anerobic systems, and not the most effective way to raise FTP.

If you have longer climbs available, do repeats of those at the highest level you can sustain.

If you don't have any longer climbs, doing 2x20 intervals on the flats, (20 minutes as hard as you can sustain, 5 minute recovery, repeat) will increase your FTP. Do those twice a week ( along with one day of your hill repeats), and in a month you'll be faster up those short climbs, as well as have the endurance to ride longer, and do longer climbs.

I just started trying to get more comfortable with standing while climbing, when I first started It felt so irregular and unnatural but im slowly getting more comfortable with it and using it more often.

I can easily add that to my routine.
This is the usual loop I take when I go for a ride, has bike lanes the entire way around the lake.
https://www.strava.com/segments/750082

Spin class. You can do standing, sitting interval pulls, ten minute max efforts. If you bonk in zone 5, you just stop. Being a oldster I'll pass along the warning that your development of your awesome climbing ability may come at the expense of flexibility and muscle balance. As a newbie but serious yoga practitioner I am in shock that I dealing with the flexibility of a life long couch potato, or heavy weight lifter.

Hill training.

Find a nice hill nearby. Ride up hill. Coast down hill. Ride up hill. Coast down hill. Repeat until exhausted. Limp home.

This is great advice. I live in an area with relatively short but steep hills and doing what merlin is recommending has helped me improve on those short/steep climbs. Riding those climbs over and over again is fine, but the interval of hard stress is too short to be hugely meaningful.

I wish I had mountains to ride up...but don't.

ftfy. It's all about attitude, I think.

A lot of the advice out there is to sit and spin a low gear on hills and avoid going into the red, but that's never had much value for me. Intentionally attacking every hill out of the saddle with a gear that makes it a challenge, now that's what whipped me into shape in a hurry and got me to enjoy hills. YMMV. Congrats on the weight loss, too.

I am also a new cyclist (4 months or so, ~800 miles) so take my advice with a grain of salt, but I have seen a lot of improvement on hills over that time-frame. There are a few things that I have focused on while climbing that I think have helped me.

First is, learn to use the full pedal stroke on hills; 360 degrees of power from both legs.

Second, sit up to expand your lungs and take long deep breaths. I have found taking long deep breaths helps me conserve energy and allows me to get the oxygen to my legs that I need. Sitting up with your hands on the tops or the hoods will expand your lungs a bit and allow you to breath easier. No need to be aero when riding up a hill.

Third, do more hill repeats and use those repeats to experiment. I start my repeats in the lowest gear and spin up the hill. Then next time up the hill, I increase one gear. I continue increasing the gear I use on each subsequent repeat. In addition to training both spinning and strength, I think this exercise has really helped me understand my gearing better. It has taught me what level or resistance gets me up the hill fastest, and what level of resistance gets me up the hill with the amount of energy exerted.

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On a side note, huge congrats on the weight loss! I am on a similar journey myself, also 6'2. I am down to 190 from 245 with a goal of 180. When I started cycling I was at about 230 so loosing all that weight is probably the biggest factor in me getting better at hills.

Thank you, and I dont necessarily hate hills, I just want to get better at them.

Ill definitely keep that in mind, using the full pedal stroke has actually helped me a bit, but I have a weird habit of just using the upstroke when my legs start to get tired to give my other muscles a break for some reason they seem to have better endurance.

I have always approached hill climbing the same way. (BTW, I am 205 lbs.) I focus on keeping my cadence consistant, and staying seated.

My training involves approaching the hill at a steady cadence, and shifting when my legs start to strain (before they are toast). I shift to maintain cadence regardless of the speed.

As I progress (this is good for repeating the same hill) I try to avoid shifting longer and longer.

You can use your shift points as a marker for improvement, and after a few cycles of this method, the hill gets easier and easier.