i would simply suggest the pill to him for obvious reasons..sometimes pride takes preference over pleasure especially among us older curmudgeons..

Of course tell him-get the literature-go over it with him-it is ridiculous to pass on a hard dick when for most folks with the issue it is so easily corrected...........

try to bring the issue (dare I say up) in the right way.  Only you know what is best.  
Gals have been helping guys in every imaginable way for millennium, and for that we are thankful.    He'll most probably be grateful!    Lucky guy, by the way!!

I have a similar problem. I cannot maintain an erection when I recline, yet can still cum, so I rely on oral or hand stimulation. ED can be caused by many different things. Blood press. meds, cholesteral meds, daily aspirin, venous leakage, etc. I've tried every pill to the max dose, and injections. Nothing worked, because of above meds I have to take. I'm seeing an ED urologist next week for any options, implant? So sometimes it is not as simple as a 'little pill', especially if taking meds. Yes he knows about it, yes he is frustrated, and yes he would welcome the conversation and support. This effects both of you, both of you need to address it. Good luck! PM ok

If you care about him as much as you say, and if you are right that he cares about you, then you should talk to him.  With kindness and care you can make him understand it's something you both need to deal with.  If he's as much of a man as you think, he'll deal with it.  If not, you'll find out what you need to know to end things.

My wife convinced me to try it since I wasn't doing it for her at that time. So I say let him know there are options. Have him talk with his doc and go from there.

If this was a provider/client relationship, even a very close and long term one, I'd be less certain.  For example, he must be aware of the medical options, and has perhaps tried them to no avail, and now wants acceptance and pleasure from a provider.  It could be very alienating to have to hear from the provider that he is inadequate.  The safer course would be to keep mum.

But since you are a close friend/lover, you should be able to bring this up to him, and I hope that something very positive comes of it.

He surely knows he has a problem.  He probably doesn't know how to talk about it.  Many guys with ED have a very hard time talking about it.  Don't be surprised if he has trouble talking about it.

BUT, Ed has many possible causes, some of which are medically very serious.  He should be thoroughly evaluated medically.  Did you know that ED is a better predictor of heart attack and stroke than high cholesterol or high BP? Diabetes is a major cause of ED.  The list goes on.

franktalk is, IMHO, the best site around for guys (and their female partners) to learn about ED and to discuss it (anonymously or not) with others who have been through the same issues.

Like you, nothing worked for me.  Went to 3 different 'experts', professors at major medical schools who specialized in ED.  Tried everything.  Ended up with an implant 3 years ago and I love it.  franktalk.org is a great resource for anyone trying or considering the more advanced options.... implant, injections, VED.

of other health issues.  

I'm on a basket full of meds for a chronic medical condition...  the progressive neurological damage will eventually put me in a wheel chair.  But not YET.  The (FM) Neuro who told me to pick out my chair 10 years ago, got flipped off to her face & I found a new Neuroologist.  I can walk a bit still with a cane or support.  

Back to the topic, I can get away with small doses of Viagra or Cialis...  I'm taking the Cialis every other day for BPH & doing well on it.  If I get a chance to play, it's enough for function.  
My MD who prescribed (first V & later C) told me there's no magic in the coatings except the taste factor.  I could get several bangs out of a 1/2 50 mg V.  My MD only Rxs 100 mg V because they cost about the same & he told me to buy a pill cutter.  For me, 25mg, 50mg, 100mg V all worked the same & minumum doses had fewer side effects like congestion.  
I had Cialis backaches with full doses but do fine with the daily.  

Approach this gently.  ASK, don't tell.  Has he talked to his doctor?  He doesn't want to give up, clearly.  Then at least get the check up.

END OF MESSAGE

Tell him, in a playful voice, "You know, a lot of people use this, it's supposed to make everything more...everything."  Don't mention anything specific.
I've done that before and got happy (you're so thoughtful) tears followed by giddiness.  When he saw that it worked and that I didn't think it was weird or awful, he did go to a doctor and get a prescription for himself.

I keep it around now.

Get a printout of "Do not use if:" for him to look at, but it's a really safe med.  If you'd like more specific info, you can pm me.

Great Thread... As I am also challenged by ED... V causes heartburn for days.... C did the same thing, but then I just said screw it and took OTC Heartburn meds... However, I am still trying to figure out the right combo to get it to work well (main reason for hobbying... LOL). Just REALLY hoping it's not low libido or low self-esteem because I love beautiful women... Or any woman willing to get neked with me and rub on me. Yes, I DO know my inadequacies. I hate spending hard earned cash to hobby and not be able to get off, or have a semi-stiff O. Seen the MD's.

Oh, well... Keep trying.