I very strongly believe every couple should talk to a lawyer to find out what the default state-written prenup says for their state so that you can accurately determine if a custom prenup might work better for your situation. Maybe it would, or maybe the default prenup is fine. Most people don't realize they're agreeing to a prenup one way or the other though. But you should fully understand the most important and far reaching financial legal document you'll ever sign in your entire life. You can just pay for an hour to understand the basics for your state, and if you decide to do a custom prenup then it'll be a few hundred more but then you both can feel safe knowing you're each protected. Sometimes there's some very surprising things in the default prenup, as I learned the hard way when I got divorced even though I never in a million years thought I'd ever get divorced. But shit happens sometimes.

So for things like the debt, in some states you'll become legally responsible for any future debt your spouse racks up. Spouse racks up $50k hidden credit card debt during the marriage? Well you're now legally responsible for $25k of that if you decide you can't deal with drowning in debt anymore even if none of it is in your name.

Anyways other than that, make sure you fill out the W4 for this year as if you were married because when you file your taxes next year you'll be considered married for the whole 2023 year. But also be aware that if you fill the W4 as "married" the form will by default assume only one of you is working. So you either need to allocate extra with holding (the calculator will walk you through it) or just select "single" to ensure you don't under withhold for 2023.

The biggest thing is just making sure you're on the same page about money. That you both (hopefully) prioritize saving and retirement and not spending frivolously. Because if one is a saver and one is a spender that's going to make something that should be quite easy (marriage) into something that is quite challenging.

That's just incredibly risky. And considering the last risk you took (marrying this person) didn't work out, then that's not really great odds.

It's one of those things that theoretically could work out OK and I get why you'd both consider it, but I'd just chalk it up to the cost of divorce and make a clean break. Unless you could literally make it a term in the divorce decree that she does pay you or something, but I doubt it's possible and enforcing that would be a massive pain. I'd do what your lawyer suggests, that's why you pay him.

I haven't mailed in a bill in years except for child-care which was hand-delivered. It's all online or automatic payments. Anything not on auto payment I designate a specific day at the end of the month to pay everything.

Almost every utility lets you auto-bill against your checking account. Almost everything else can be put on a credit card for the points and then auto-paid.

It's pretty typical that that's the best way to get paid the most the quickest. But it actually is also possible to stay and still get paid well.

I've been tracking my total comp since I started and on average I've gotten a 9.4% raise each year. Some years lower (looking at you 2009 where I actually went negative YoY but lol at finding a new job), some years higher, but that's the average I've had from sticking with the same company for the last 16 years. I have of course gotten lots of interest from other companies but either the new job sounds worse or they can't significantly (>20%) beat my current salary at the time so I stay put because I still really like my job and my coworkers and location. Also the same reason many of my coworkers are also still here even longer than I have.

Anyways as long as you're semi-regularly checking to make sure you're still being paid well compared to jumping companies, then it's not necessarily inevitable you'll get paid less, but I'll admit I'm probably more of an outlier.

And FWIW people have been saying "20 years at the same company days are now over" since the 1990's so it hasn't been true for a long long time.

What's the car? What is your current car? How much is your current insurance+gas? What are the terms of the loan (interest rate and length and loan amount)? What is the total cost of the car? What's your down payment? How much is in your savings today?

Do you currently and consistently have an extra $1k ($300+$650) left over at the end of the month, what are you doing with that money today?

Assuming you can sell the stock immediately after it vests (usually every 6 months), there is not a downside. Basically you're putting money in an account to buy company stock at a 15% discount at the end of the 6 month period. So when you sell it, you should see an immediate 15% profit on that by selling it immediately. The exact amount may be slightly higher or lower depending on the specific stock price it was bought at vs the price when you sell, but if you sell the stock the day you get it at market open then that difference will usually be very negligible.

Yes you have to pay some taxes on that 15% profit, but that just makes it a 12% net profit. If you can deal with the cash flow reduction for the first 6 months then it's absolutely worth it because it's free 1.5% bonus (assuming 10% of salary with a 15% stock price discount). After the first 6 months then you can just use the previous money to "pay yourself" to make up the gap, and then there's not even a reduction in your income. It's also a nice enforced savings mechanism.

Most of the negatives are only pertinent if you're required to hold the stock for some period of time before you can sell it. Or if you just decide to hold the stock for some reason and don't sell immediately.

You just need to clarify when you actually get the bonus. Because there's two types:

1. You get the money in the next paycheck or two. It's a "Thank you for not quitting on us" gesture of good will with no strings attached.
2. You get the money one year from now (in Oct 2023) so you have to stay on the job for another year until you get the money. This is much more common for "retention" bonuses and why you found this type more often when you did your Googling. Often the timeline is actually spread out over multiple years so you get 1/3 after one year, another 1/3 the 2nd year, and the last 1/3 the 3rd year but it can vary drastically so you'd just have to check with your boss. I have had 1-year get-it-all retention bonuses like this, but is just more rare.

Both are very normal business practices to retain employees and keep them happy. I've gotten both types in my career.

Since it's only $5k and he said it was "no strings attached" then it's probably the first type but just talk to him and clarify it.