The complicated reality of security arguments for season 3
A lot of arguments I've seen about why Pen should have married Debling includes Portia being right about how it promised "security" (implying more security than Colin could provide) and how is they were Penelope they would have "gotten that bag" and been "practical". Let's get into the more complicated bits of this regarding characterization, realities of this arrangement, and nuance. (TL;DR at the bottom of the post).
Characterization of the main players
Penelope:
Penelope is characterized as a hopeful romantic with a pragmatic side when necessary. She might lean more towards stoicism than loud outbursts of emotion with people she doesn't trust herself to be vulnerable around, but that doesn't mean she doesn't feel deeply. She isn't the type to hold grudges, it goes against who she is as a character.
A lot of people argue that Colin and Eloise should have had to "work harder" and Colin should have had to "grovel more". There's this idea that in order for Penelope to be this strong independent female character she has to fit this rigid idea of a "girl boss". The girl-boss-ification of Penelope Featherington is something I find to be regressive because it often goes against everything Penelope represents as a character.
Penelope is a perfect example of a strong, independent, flawed, complex female character. How often do we, in this day and age, get a female character who is presented as being strong and independent but who is also kind, hopeful, forgiving, and deeply feeling? She's not a stone cold bamf, she's not an angry character who holds grudges, she isn't an unfeeling business woman, she's more nuanced than that. She's human, she's vulnerable, she's kind, she's mean and vindictive in the way a lot of teenage girls are. She regrets it when she hurts other people, she forgives easily because her love for the people close to her is more important to her than holding grudges against them.
This is a girl who grew up in a cold, unforgiving household with parents she likely felt didn't care about her. Her father was an emotionally distant alcoholic and gambling addict who wasn't present even when he was in the room. Her mother was a social climber who viewed Penelope as a lost cause in the marriage mart. Her sisters saw their mother criticize everything about her and joined in, likely in hopes of receiving positive attention.
She's hurt, feels invisible, and is deeply insecure. Whistledown gave her a voice and a feeling of being important that she didn't have anywhere other than with the Bridgertons.
Penelope likely wouldn't have gone through with marrying Debling even if Colin hadn't gotten involved. Unless her mother forced her. It went against who she was and she very clearly struggles with it and the idea of an amicable marriage where she would be alone, the one thing she has spent so long trying to escape.
Debling:
Debling is characterized as a fine man, safe, passionate about his interests, but detached from personal relationships. Not an ideal for a match with a romantic. He makes it clear that he has no interest, and likely no capability, to form a deeper attachment than simply an amicable acquaintance.
He's pragmatic in what he's looking for in a match, and wants someone who will be fine on their own with separate interests from his own.
Really not much else is known about him than that.
Portia:
Portia is characterized as a pragmatic social climber who simply wants to marry off her daughters into logical matches. She isn't feeling and warm, nor open in her care for others. Her daughters stuck dealing with the brunt of that closed off nature.
She is uncaring about how her daughters feel about whatever match they make as long as it's secure. She nitpicks every perceived flaw they have and brushes it off as wanting what's best for them. She loves her daughters but is incapable of providing them with the emotional support they need.
She doesn't support Penelope and Colin's engagement when she discovers it not because she thinks it isn't secure, he is a Bridgerton after all, but because she doesn't view Penelope as someone who has a love story like that.
She isn't a good mother that's misunderstood, she's a bad mother who has good intentions. That doesn't make her a terrible person, it just makes her an extremely flawed and realistic person.
Bridgertons:
The Bridgertons are characterized as loving, open, warm, and protective. It's made clear early on that Penelope is seen as a member of their family, a fifth sister of sorts. They are quick to bring those important to each other, that are serious and likely to stick around, into their fold.
They don't forsake family no matter what, it's their first priority. They take threats against one another seriously and would do anything to protect one another.
Debling family:
There is not much to go on here other than what is mentioned by Debling in one offhand remark. What we know is that there doesn't seem to be love lost between him and his family and that they would prefer to have the title. It's one of his reasons for finding a wife.
The realities of the situation
The marriage itself:
They'd have barely anytime together before he left, in all likelihood they'd at most be decent friends by the time it was time for his trip. They would have no contact for 3 years, and best case is she's alone and pregnant with a son during that time. There would be no way for them to have contact with each other.
The inevitable conclusion:
Penelope would be a married woman and current countess for, at most, five years. I give it that long before before they stop viewing him as lost at sea and actually consider him officially dead and her a widow and dowager. That's if no one somehow learns of the ships destruction sooner. The first successful voyage along the northwest passage was almost a century away.
The complicated aftermath of being widowed:
Here's where Penelope hopefully being pregnant with a son comes into play. If she gives birth to an heir she becomes the interim Countess until her son comes of age. If not she is entitled to dower rights, this is where things to get complicated. She would not have been able to be Debling's heir as she could not inherit an aristocratic title or the associated estate, unless they were in Scotland where such a thing was a possibility (likely the reason they chose Francesca for their queer love story as Michaela would be able to inherit).
Contrary to popular belief women of the time could, in fact, own their own property, just not aristocratic property (outside of Scotland as previously mentioned).
Let's say the marriage contract had no jointure and there was no entail, Penelope would have Dower rights, meaning she would have a life long interest in one-third of her deceased husband's estate and access to the properties until her death. This was not ideal for a lot of reasons as things often got complicated for the heirs, especially if there were multiple dowagers from different generations, and the dowager's allotment was dependent on how prosperous the estate was.
Now, I imagine Debling or Portia would, as was most common, decide that a jointure would be best as to ensure a simple and more straightforward process/more secure arrangement. A jointure could be seen as a refund of sorts and is often payed using the widow's dowry. A jointure is an agreement established within a marriage contract for a fixed yearly allowance for the woman after her husband's death. It wasn't uncommon for the amount to end up not being enough to properly support the widow and leave her in a precarious situation due to whatever reason. A bit of a gamble but sometimes the more prosperous and safe option.
The reason I say safe is due to the special nightmare scenario for a young lady of the time: marrying into an entail. This case would definitely result in Portia insisting on a jointure due to the risks. An entail ensures that no heir can be named by the owner of a property as it was already set to go to an heir, most commonly the eldest son of the property owner. If there was no son it would them pass to the closest male relative. Without a jointure a widow was left entirely at the mercy of the heir as she could be denied dower rights, which was legal in the case of entails. A jointure was slightly safer but still risky as it could not involve any part of the estate tied up in the entail, meaning the husband would either have to:
Provide the money from any funds he had not involved in the entail or hope for a large enough dowry from his bride to posthumously support both her and a possible widow from the last heir. There is also the fact that should an estate go into debt, entail or not, the jointure no longer applies and the widow is left on her own.
In short her being married to a Lord basically meant she was dependent on either
A.) How prosperous the estate was that year
B.) A fixed yearly allowance that's determined by the size of her dowry (which given the Featherington financial situation might not be the largest)
C.) Whether the next Lord avoided going into debt (which is a serious risk given the fact that they're only a generation or two away from the need of the million dollar princesses)
D.) Possibly, in lack of a jointure and existence of an entail, penniless/at the mercy of a man she does not know from a family that doesn't seem fond of her husband.
(All this makes her using her Whistledown savings slightly riskier after Debling's death and might draw attention).
Colin is a safer bet, a known entity with a family that would never even think of not supporting her to their best ability, likely beyond any dower rights or jointure. It's also literally canon that despite Colin only being the third son of a viscount he is, by virtue of being a Bridgerton, literally better off financially than some Earls. It's an actual possibility that he's fiscally a better and more secure match than Lord Debling.
The only thing Debling can provide that Colin can't is a title. Colin on the other hand can provide a marriage filled with love and happiness, a family that will always support her, and likely even more financial security than Debling.
I'm convinced Portia's concerns weren't due to actual doubts about fiscal security, but because she didn't think Penelope could retain Colin's affection for the duration of their engagement.
TL;DR: Colin was actually the safer and more secure option due to a lot of real world issues regarding the realities of being widowed in the early nineteenth century. "Security is romantic" actually applies to him because he likely has more money than Debling and his family would likely more than provide for Pen in case he died.
