Did the Ironborn lords ever arrange marriages with lords from the main body of Westeros, before or even after Aegons conquest?

[Rossze]

It would it feel odd and correct if they hadn't. Correct in that their culture is put off by things of this sort, but odd that they may have been so dependant on their naval dominance that they would not secure any alliances. I mean surely the Greyjoys would've realised that wars go beyond simply having a large navy after their failed rebellion?

[Vaith]

Before Aegon's Conquest

• Harmund II Hoare married Lelia Lannister. Their children were raised in the Faith of the Seven and her elder son, Harmund III, opposed thralls, salt wives, and reaving. However, her younger son Hagon Hoare rose up, restored the old ways, and sent Lelia back to Casterly Rock, mutilated, which outraged the king and led to a war where a westerman briefly became King of the Iron Islands

After Aegon's Conquest 

• Early in the reign of Aegon I, a marriage was arranged between a Tarth daughter and a Harlaw to strengthen the links between different parts of the realm (her triplet sisters married a Corbray and a Hightower).
• Lord Quellon Greyjoy married the daughter of Lord Piper as his third wife, who brought a maester with her to Pyke. She died in childbirth having a stillborn daughter.

These are the only known examples, which does make it seem rare, and definitely rarer than other regions intermarrying. However it is rare to know the spouses of a lot of ironborn rulers, so there could be other, yet-as-unknown examples

[Thomaerys Velaryon]

On 4/23/2020 at 6:25 PM, Vaith said:

These are the only known examples,

There is one more, Ser Harras Harlaw's mother was/is a Serrett from the Westerlands.

[BlackLightning]

On 4/23/2020 at 12:25 PM, Vaith said:

Before Aegon's Conquest

• Harmund II Hoare married Lelia Lannister. Their children were raised in the Faith of the Seven and her elder son, Harmund III, opposed thralls, salt wives, and reaving. However, her younger son Hagon Hoare rose up, restored the old ways, and sent Lelia back to Casterly Rock, mutilated, which outraged the king and led to a war where a westerman briefly became King of the Iron Islands

After Aegon's Conquest 

• Early in the reign of Aegon I, a marriage was arranged between a Tarth daughter and a Harlaw to strengthen the links between different parts of the realm (her triplet sisters married a Corbray and a Hightower).
• Lord Quellon Greyjoy married the daughter of Lord Piper as his third wife, who brought a maester with her to Pyke. She died in childbirth having a stillborn daughter.

These are the only known examples, which does make it seem rare, and definitely rarer than other regions intermarrying. However it is rare to know the spouses of a lot of ironborn rulers, so there could be other, yet-as-unknown examples

The example of Leila Lannister and Harmund Hoare is a damning one if I must say so myself.

I would be extremely reluctant to arrange a marriage between my daughter (or even my son) and Ironborn nobility.