His best choices are either Supergirl (Kara Kent), Batgirl (Barbara Goordon) or Wondergirl (Donna Troy).
Lets analyze each of these women.
Lets Star with Supergirl when through most of Supergirls stories she is always seen as a teenager. If Peter or Kara did get togther Peter would have to be a teenager again think like how he was in Ultimate Spider-Man. Now the best thing is Supergirl is someone he dosen't have to worry to much about I'm pretty sure if Goblin threw her off a bridge it wouldnt be to bothersome for peter. Kara also has someone who wouldnt be stupid enought to seel her relation ship with the Mephisto, but the problem is she can be too powerful and anydrama is something that can possibly happen, but not as often. So sadly unless all of Spider-Man's enemies had more Kryptonite based attacks which wont mater as long as Spider-Man is around.
Now lets look at batgirl people say she is bassically MJ, but looking at it I think Barbara gordon is more simuler to Gwen Stacy. Don't believe me her alterego is a female counter part to the male hero, they both extreamalky intelligence, and both have a father who is a poilice chief. Now unlike with Kara, Barbara is someone Peter would worry about her, but like Kara she wouldn't be stupid enough to sell her marriage to Mephisto, but unlike Kara i fear she would be in more danger keep in mind When I refreced the death of Gwen Stacy I was refering to Kara by her idety Kara not supergirl, but barbara its more dangerous especially when later with what happens during the Killing Joke. How ever this is good mainly because Peter would be more concernfor her, but a little to concern. so I say she is possible.
What about Donna Troy well here is the thing with her you see Donna troy has had a hard romatic life, Just like peter did so the Drama works, both are probably equal in abilites and their kind heart, pluse when people talk about being paired with Supergirl or Batgirl thats a n automatic justice leauge thing. Now with Donna its diffreent because she has been around teenagers who can relate to both her and peter.
So I am going to go with Donna Troy She is verystrong like supergirl and can fly, but she also is more concern and the drama between both her and peter is more balanced.
So for Spider-Man's pick im ganna go with Donna Troy, but for Batgirl i am going to pair with Spider-Man also but its Miles Moralise version, and for Super Girl ill pair her with one id the scarlet spiders.