I really hate to be the newbie who immediately heads over to the "free advice" section, but I really need some guidance here.

The absolute love of my life is a Scorpio Asc, Libra Sun (11th house), Capricorn Moon (2nd house). He was my boyfriend/roommate/best friend for 3 years, 2 of which we spent engaged. Our relationship was virtually effortless and no one has ever made me feel the way he did/does. We were very, very young though (19-22) and I felt like I still had some "living" to do, so I broke it off. The breakup was really difficult for both of us, and the "living" I ended up doing afterwards was just really damaging. We've kept in touch over the years, and every time we get close the old spark comes back just as strongly as it was in the beginning. The timing, though, has never been right, and each time we've had to separate ourselves from each other because one or both of us was with someone else. There's so much romantic tension between us that sometimes I don't even feel like I can be around him, yet we never EVER address it directly. We just sit on the tension and hope the other will say the words. 

Recently, he asked me to begin a new musical project with him, which means we'll be spending at least two nights a week together practicing and recording. He only recently broke it off with his girlfriend of three years, about 5 months ago. For the first time in a long time, we're both single. But here's my issue: how the heck do I proceed?

I doubt he would ever make the first move- historically, I've always been the one who did all the instigating/leading (Aries) while he hung back and made sure everything went smoothly (Libra). But life has gotten a lot more complicated for both of us in the past few years, and I have a child now from another man. He's met my son, and they get along, but I have no idea how he really feels about the situation in general. He also just left a serious long term relationship with a triple Sag (Asc, Sun & Moon) who was psychically abusive (I witnessed this first hand many times), and the experience has shoved him pretty deeply into his shell. We're both sort of limping around now, stuck in limbo, and I don't want to make a move if it's the wrong time. If we ever got back together, I'd want it to be forever. I'd rather have him in my life as a dear friend then risk losing him completely to drama/circumstance later on.

Transiting Pluto was crossing my Descendant when I left him, and it's just now (finally!) leaving my 7th house. I know the timing is right for me, I feel it in my bones. But I want to proceed with caution, for his sake and for the sake of our friendship. Is it possible to love someone SO MUCH that you completely stunt your own intentions trying to do right by them? It seems like that's been going on between the two of us for the longest time.

Now that I'm done babbling, here's some more info on our synastry:

Suns (Aries & Libra) opposite by sign, but not degree.

Moons loosely conjunct in Capricorn

His Sun conjunct my Mars in Libra

His Venus in Virgo opposite my Venus in Pisces

His Venus trine my Moon

His Mars (Sag) almost directly conjunct my Uranus (0° 08')

His Sun tightly sextile My Uranus (0° 51')

Our Mars' (Sag & Libra) directly sextile (0° 0')

Both of our Suns in each other's 5th houses

His Moon in my 8th house, my Moon in his 3rd

His Venus in my 5th house, mine in his 4th

(Synastry chart below as well) 

We both have many positive transits going on right now, but transiting Saturn is going to start crossing his 11th house of Libra in a few months, which he has a LOT of planets in. Should I hang back and wait to be a rock for him in times of need, or is time to just STOP hanging back once and for all?

if you post the chart(s) or link to them and someone will post them for you - people will be more likely to respond.. :-)

welcome, luna mile! 

Honesty, it sounds like a really compatible match to me. No need to see the chart!

I would vote for you making the first move (or at least sitting him down and saying "Hey, now that we're both single again..."). You guys have waited enough, and I'm not sure if I'd want to wait any longer in case life throws another curve ball in there and you NEVER get a shot at him again.

Yikes, thanks Elsa! I'm Mercury ruled, you know? I always think that lots (and LOTS) of words will work, haha.

Here's the synastry chart- I'm on the inside, he's on the outside.

Hi kashmiri! Thanks for the welcome! I really like the vibe here, everyone seems so nice/knowledgeable.

jenfullmoon, I know exactly what you mean. I also have this tendency to completely jump the gun when it comes to relationships. I care for him so much that I step all over myself, which is really uncharacteristic of me! I keep thinking they'll be a perfect "moment"- tonight, maybe?

The ultimate doom here for us? "Clues." It seems like we're constantly throwing vague "clues" at each other but never know how to interpret them. He simultaneously seems interested in me romantically and not- and I do EXACTLY THE SAME THING. It's SO anxiety inducing! Is that a Cap moon thing?

Hm, not sure, but then again, I don't seem to know any Cap moons to judge on behavior. But it sounds like nobody here wants to go out on a limb and express interest for fear of rejection. Saturn emphasis, I guess.

indeed, aloof, cautious, self-conscious, SARCASTIC capricorn ruling emotions on both sides is hard to those trying to express where eachother stand.

both venus ruled mercury's points to a tendency of avoiding confrontation. i'd look to transits to mercury from the inner plants (sun,venus, mars, mercury, jupiter) to pinpoint a good moment to bite the big one...which i'm hoping you're convinced of bringing to actuality! your relationship sounds wonderful, you both deserve to make the most of it...and a little romance never ruined anyones day ;)

have you researched Draconic astrology? you can generate your draconic chart on asto.com, check for transits from outer planets to your draco. chart, signifying progress through your souls journey. transits to draconic planets will be deeply felt.

i've got nothing to add except welcome - and good luck.