I have a thing for emotionally insecure and and damaged Tony and Steve figuring that out and trying to help. Any fics to rec? I know that’s a pretty common thing in fics, but I was wondering if you had any particularly angsty favorites within that trope?

Try the Tony’s Insecure recs. Here are some others that you might enjoy:

DON’T BE TOO INSECURE TO LEAVE COMMENTS AND KUDOS!

Looking for Trouble by JacarandaBanyan: In a fit of insecurity, Tony builds a portal to
alternate dimensions in an effort to prove to Steve that their
relationship is doomed. Ironically, this ends up strengthening their
relationship.Or: Non-Powered AU Stony dimension-travel to various universes, including the MCU, at some point post-Civil War/Infinity War.

The First Time I Went Dancing Sober by schemingreader:
Steve Rogers is a great physical therapist who works with sick kids.
Tony Stark is a damaged biotech engineering genius who really wants to
be one of the good guys.

Hydrotherapy by @blossomsinthemist:
It was nice, floating, like this.  Not being terrified, not
worrying about it, even though the water of the pool was washing over
his belly, soft and cool at the sides of his face, damp at his temples,
at the edges of his closed eyes.  “I’ve got you, Tony,” Steve muttered,
and it was so sweet, so soft, in his ears, washing over him like the
water of the pool lapping at his body, cool at his ears, tugging at his
hair.
I wanted to write a fic about Steve and Tony having sex while Tony was floating in a pool.  So I did.

I Like You by KiwiFruitJuice:
Steve and Tony have been dating for exactly four weeks, and Steve has
massed thousands of dollars worth of gifts. In the midst of figuring out
the perfect gift for a man who has everything, Steve learns something
important from Tony.

I would Choose You by @s-horne: “I was never in love with her. Besides, you’re my soulmate.”Tony scoffed so loudly that Steve actually moved back in shock. “What does that mean?”“It means that I love you,” Steve answered Tony’s theoretical question.“No, it doesn’t. What it does mean is that the universe decided we
should be together. It doesn’t mean that you chose me or even that you
can’t love someone else.”“Tony…” Steve seemed lost for words and Tony sighed, just about
managing to refrain from rolling his eyes as he really tried not to cry.
Here it came. The rejection. The admittance that it had all been a lie,
just like Tony had suspected.

“I don’t want to screw this up” by @s-horne: “This is good,” Tony started before he groaned in
frustration when the right words wouldn’t come to him, on the tip of his
tongue but not coming out clearly enough. He lifted his hand and
gestured between himself and Steve. “This… Me and you, as we are –
it’s so good… You’re my best friend and I just feel like if it goes
any further, changes into something more then…” Tony broke off and
sighed again before he shrugged lightly, his voice full of defeat. “I
don’t want to ruin it.”/Steve and Tony finally tiptoe into new relationship territory when old insecurities make for trouble in paradise.

your heart breaks in my chest by deathsweetqueen: Steve Rogers was never more happy the day that his
soulmark came in, but it led to nothing but disappointment and shame
when his soulmate ignored everything he scribbled across his arm; as the
years went by, the reason became unmistakable: why would his soulmate
want a weak, wretched little thing like him? Tony Stark was born
bitter cold, like he was made of hailstone, and when his soulmark carved
itself across his pulse point, he realised why; so, what is his life
worth, what could it ever be worth, when his soulmate is dead and he
would never have been worthy of him had he been alive anyway?

Never, I will never leave by nads31:
Tony is insecure and Steve makes him feel better. Cute fluff.

Tony’s Heart by @neverthelessthesun: “What’s this?” Steve asked him, suspiciously eyeing the
little box Tony had chucked toward him just a moment before. Steve,
being the pinnacle of human perfection, caught it, and was now holding
it in the flat of his palm. “Just a little something I thought you might like,” Tony said as
casually as he could muster, though he tellingly couldn’t rip his eyes
away from Steve’s. “Open it.”

Worth It by @neverthelessthesun:
Tony is trying to make himself worth it to Steve. He doesn’t know where he is failing.