So oldest to youngest ....
Lashiel at over 2,100
Mab was a contemporary of Merlin (5th or 6th century wasn't he?) so say 1,400
Lara was from before portraits were popular so 500 or even 600
Luccio 210
Molly 30
He does like 'em older ...
What was it, that Harry's Alter-Id said about Luccio? "There's something to be said about experience."
On a different tack, Mab said something about Lara; which is open to different interpretations, but one of those relates directly to Harry. After Harry told Mab that she was forcing him into something that shouldn't be forced, the Queen of Air and Darkness replied,
"Yes, I am. Because I judge it necessary. Our world has just become infinitely more uncertain and dangerous. We must become stronger and more stable to face it, securing both the appearance and fact of a secure alliance with a competent partner. This is more important than any given person or their petty desires. Including yours." I think the obvious interpretation is that Mab wants to secure Lara Raith; someone Mab sees as highly competent, as an ally. However, there could also be a second meaning here. Mab may also believe her Knight needs a competent partner to work with and Lara Raith could help Harry; I not certain here, make Harry a better, more effective
monster weapon.
Mab is not trying to create a Love Connection and Harry's dates with Lara won't look like an episode of The Bachelor. I could see Harry saying to Mab, "You know Lara will try to enslave and devour me." To which Mab will reply, "Don't be ridiculous, I saw the burns on Ms. Raith. She got them touching you, didn't she? You're protected from Lara Raith and any of the other Raiths." Harry will then fallback. "You know that protection can very easily be lost." Mab: "Then you'd better hold on to it, especially as you may be married to Lara Raith for some time." Harry, "Wait, I'm going to be married to the Queen of the Succubi, but I have to remain celibate?" Mab: "You've been celibate before and you rejected the entreaties the numerous sidhe ladies who made their desires known to you at your birthday party. Really wizard, I don't see how this is any different. Plus, didn't you say that you didn't want Lara Raith to enslave you? This is the most effective way to prevent that from happening."
By the way, in a very recent interview Jim said that over the next year he will release some fiction that will show Harry over the next 12 months making official visits and appearances as the Winter Knight. Presumably Lara Raith will be at these functions. Jim didn't say if this will be a short story or microfiction.