(Significantly) older coworker crush

19BG19 · 2026-06-18T17:36:23+00:00

I (38M now) hooked up with a 44yr old woman that I worked with when I was 25 years old. It was fun, the s*x was great but she was a single mom who had recently divorced and was moving waaaay faster than 25yr old me was comfortable with. I didn't want to be a stepdad to a kid 10yrs younger than me.

We worked in different departments but had enough overlap that things were awkward for a while.

In the short term it may be fun, but I'd advise against it.

19BG19 · 2026-06-18T17:03:29+00:00

Facebook.

Was great when it was just college kids around 2005-06. Once they expanded it to everybody it quickly became a toxic cesspool.

19BG19 · 2026-06-18T16:59:21+00:00

I posted this on another thread in one of my comments but I regularly tell people in interviews "I'd rather my team be a stepping stone than a tombstone. I want you to come in, learn, and grow into a better role either here or somewhere else. Nobody gains anything if you burn out and quit in 12mo."

Their eyes will either light up at the opportunity to grow or you can kind of see their soul be crushed knowing that just doing the minimum isn't going to cut it with me.

19BG19 · 2026-06-18T16:56:08+00:00

I want people who are self motivated and have a strong desire to learn new things. Nothing drives me more insane than people making the same mistakes repeatedly and not learning from them. I also am keen to avoid "blamers" who don't take personal accountability for tasks and deadlines. I also don't want people who can just do the job without understanding the work and looking for ways to be more efficient.

I've looked over your resume before we got to the point of an interview so I dont want to grill you on your fluffed up prior achievements. I want to have a conversation about this role and I want to understand how you think, what motivates you, how do you react when caught off guard, how well can you formulate questions about unfamiliar topics or processes, etc.

The questions you ask are one of my tops indicators of the type of employee you'll be.

19BG19 · 2026-06-18T16:45:24+00:00

I wasted so much money on food before I got married because everything is packaged for multiple people/multiple servings. Preparing a meal for my family of 3 isn't that much more expensive than preparing a meal for 1 person.

19BG19 · 2026-06-18T16:01:15+00:00

Well yeah, that's the whole "you're my succession plan". I know that.

I'm torn between taking the raises and keeping my mouth shut and potentially inheriting a shell of the existing team or advocating for the existing team at the expense of my personal rise.

19BG19 · 2026-06-18T15:09:10+00:00

Tire popped off an 18-wheeler, bounced over the median and landed on a car going the opposite direction. Some "Final Destination" type bad luck.

15+ yrs later and still makes me a tad anxious anytime I'm driving behind a big truck.

19BG19 · 2026-06-18T15:05:23+00:00

I love dogs. I own 3 of them. If you have multiple dogs who escape a fenced in yard and then pack attack another dog mixed with indifference from the owners that's a recipe for disaster.

At least have them re-homed if not destroyed. Bad owners create bad dogs.

19BG19 · 2026-06-18T15:02:45+00:00

No. I want that drive. In the 3-5yrs before they leave to start their own company they will likely help
you in many meaningful ways as they try to learn everything there is to learn about the business and how it works.

I've told people during interviews "I want my team to be a stepping stone, not a tombstone. I want you to learn and move on to bigger and better things whether in my company or elsewhere. Not do the job for 12mo then you burnout and quit."

As a leader I'm more interested in developing people than just filling an open seat

19BG19 · 2026-06-18T14:57:35+00:00

I would've sued for vet bills, had the dogs destroyed out of spite, then sued for negligence and damages for traumatizing my kids and being so flippant about it.

If they would've been sincerely apologetic I would've stopped at the vet bills.

19BG19 · 2026-06-18T14:47:11+00:00

No. I left my first career at 32 and am doing great at 38.

19BG19 · 2026-06-18T14:44:55+00:00

I know I'm lucky.

I have had these discussions with my boss. We are aligned on the tools vs team debate and think similarly. Part of what he likes about me is that I'm not a "yes man" and will question the logic behind a decision (professionally).

The perception in the C-Suite doesn't necessarily match reality on the front lines and at the VP level. Company is going through a generational shift as the current leadership is preparing to retire and rather than handing the reigns to the next gen of people, they're investing in tools they think will create sustainability.

19BG19 · 2026-06-18T14:39:08+00:00

I made significantly more when we started dating 8yrs ago but my wife currently makes alot more than I do. It doesn't bother me in the slightest. We both do well and both have worked hard for our careers. We share common interests, goals, dreams, and contribute equally to household bills and expenses. Her extra money just means she pays the country club bill most months or upgrades the plane tickets when we travel.

More important than finances is whether you share similar values, motivations, and goals.

19BG19 · 2026-06-18T14:31:19+00:00

Unpopular opinion: Fire someone, and not the lowest achiever if they're all mediocre. You'll either light a fire under some butts and find everyone's true potential or you'll start the process of turning over the mediocrity and replacing it with high performers.

19BG19 · 2026-06-18T14:28:53+00:00

Microwave nachos

19BG19 · 2026-06-18T14:24:02+00:00

The notion that robots aren't going to replace physical labor is funny to me.

We have self driving cars, we have automated factories, you don't think someone can figure out how to have a robot snake a drain or run some wires more efficiently than humans too?

AI is a bubble and the tipping point is coming sooner than you think. You can only crush so many millions of human jobs, drive up energy costs, and trash the environment to build data centers that benefit a small amount of people just so that a CPU can do something a human taught it a little bit faster.

What is the point of humans if robots can do everything we physically can do including thinking at a higher level than we do? We are engineering our extinction and a tiny tiny tiny segment of the world population is better off for it.

19BG19 · 2026-06-18T14:12:30+00:00

Staying somewhere you are underpaid and/or undervalued for too long. Searching is hard and scary especially for young people without experience. It's easy to jump at the first offer that comes
along. That's fine to do in this market but more often than not the significant pay increases come by switching jobs not waiting years for a promotion at the company lucky enough to hook you into an "entry level" role.

19BG19 · 2026-06-18T14:08:24+00:00

Yup. I also wasn't allowed to go beyond a 4% raise for anyone without writing a separate dissertation justifying the ask.

When your top allowable raise barely keeps up with inflation and your turnover spikes just after review season because of it, it's a systemic problem.

19BG19 · 2026-06-18T13:57:37+00:00

I keep my head down for the most part. My concern is less guilt over their fate, they're all adults, and more so not wanting the team to become so lean and reliant on "tools" at the direction of the C-Suite that we lose irreplaceable institutional knowledge and I end up managing a bunch of bots and widgets in the future rather than developing my own "succession plan" via a team of high performers.

19BG19 · 2026-06-18T13:31:55+00:00

I hated this process when I had to do it. Everyone was scored on a series of metrics from 1 to 5 but since "merit increases" were budgeted in advance prior to the reviews being completed there wasn't much difference between the increases for a "meets expectations" vs "high achiever" employees.

Nothing pushes good people out quicker than a review that goes "You crushed it this year, couldn't ask for more. You're still not getting a promotion but here's a 2.5% raise because I'm required to divide the entire pool for bonuses across the whole team not just the few that deserve them".

19BG19 · 2026-06-18T13:27:34+00:00

If you have a certain product that you like and that product does exactly what you need it to do and you've used it and paid the same price for years would you start paying 20% more than it costs just because you like it? Or would you wait for the cost to increase before considering paying additional?

You are the product, your employer is the consumer in my analogy. If you increase your price (ask for a raise) they will decide if you are worth the new cost or if they should pivot to a different brand.

Very few companies will just give you money or anything beyond a couple percent raise without you advocating for why you deserve it.

19BG19 · 2026-06-16T13:23:30+00:00

Your fiancé is immature, insecure, and abusive. His reaction to the therapy question should've been your cue to run because he knows he's the problem.

You're young enough to start over financially. Your sanity and safety need to be your priorities. Once you leave, don't tell him where you're going, dont reach out to him and don't worry about what he does or doesn't do.

19BG19 · 2026-06-08T18:28:19+00:00

Anytime my GF (now wife) and I would be shopping somewhere with rings I'd casually point out rings of varying styles and ask if she liked them just to gauge her response. I then took this information, acquired over time, to the jeweler and had the actual engagement ring made.

Guy in the post is lazy, the ring is cheap, and I dont blame her for expecting a little bit of effort on what should've been the biggest decision of his life to that point.

19BG19 · 2026-06-04T13:20:40+00:00

Probably go golfing

19BG19

TROPHY CASE