‘It’s important to me because I am changing careers to be able to retire’: New boyfriend pushes 53-year-old woman to prioritize a Thanksgiving trip to Colorado over her classes, kids, and long-term retirement plans, so she cancels to protect her future

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Etai Eshet • Editor
Dec 1, 2025 5:00 PM EST

Thanksgiving road trip sounds romantic until the itinerary starts sounding like a stress test. New boyfriend of three months wants a California to Colorado drive, a pickup in Nevada, a 3 a.m. departure, four days total on the road, and a first meeting with his kids, grandkids, and not‑yet‑ex wife squeezed around an intensive statistics class with quizzes and a final right after. The plan relies on car Wi‑Fi, homework in a moving vehicle, and studying in his son's office while everyone else bonds over turkey.

The bigger picture makes the whole thing even more lopsided. Career change and that stats grade are tied directly to future income and the ability to retire at all, while the boyfriend already has a pension, a clear six-year countdown, and a prenup conversation on the table. He brings financial stability and a protected exit plan. She brings a second act that absolutely cannot afford a blown semester. Toss in the fifth anniversary of her father's death and the fact that her own kids will now be in town, and suddenly this is not a fun adventure, it is a collision of obligations.

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  • I (53)F My new boyfriend (56)(M) wants me to go on a road trip to Colorado for Thanksgiving

    Frustrated woman sits in the passenger seat during a long road trip while the man driving focuses on the road. with aquote: "We would have been driving for 4 days total round trip to spend two days in Colorado"
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  • My new boyfriend (we went on our first date August 29th) asked me to go on a road trip to Colorado to meet his children and grandchildren about a month ago.
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  • My children were originally planning on going out of town for Thanksgiving and he didn't want me to spend the holiday alone.
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  • I originally agreed to go but have now bailed. I didn't think of all of the details involved prior to committing to go.
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  • The first would be that I have school on Wednesday night and although my class is online, it is a statistics class which is very intensive and confusing to me.
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  • We will have two quizzes that evening and will be learning new concepts that will be on the final exam which is the week after Thanksgiving.
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  • A middle-aged couple sits in a car looking frustrated and worn out, each leaning on their hand as they stare out in opposite directions.
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    Image is representative only and does not depict the actual subjects of the story.

  • I also have at least 10 hours of homework to complete that week. He said that I can use his sons office to do my homework while we are there but how will that look if I am meeting his children and grandchildren for the first time and all I am doing is studying and homework while there?
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  • The plan was to drive from CA (leave around 2pm) to NV (arrive around 9pm) on Tuesday, pick up one of his sons, spend the night there and then wake up at 3 am to drive from there to Colorado.
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  • What the boyfriend frames as sweetness, not wanting her to be alone for the holiday, lands more like overreach. The relationship is still new. The divorce is only just moving. The emotional stakes of meeting his family are high, and his solution is to bend her education, schedule, and grief around his ideal version of Thanksgiving. That imbalance is the whole point. Saying no here is not cruelty or selfishness. It is a very reasonable reminder that a three-month situationship does not outrank a degree, existing family, or basic mental bandwidth.

  • His plan was for me to do my homework while on the road and he has Starlink connected in his car.
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  • He originally also wanted me to log into class while driving and take the quizzes as well on the road.
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  • A middle-aged couple argues on a quiet tree-lined road, with the woman turning away as the man gestures in frustration.
    via Prostock-studio

    Image is representative only and does not depict the actual subjects of the story.

  • He also realized that attending class while driving might be an issue so he said that we could instead drive all the way through the night and just pick his son up in NV and make it to Colorado before class so I can attend school when we arrive.
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  • He even took me on a test run to see if I could do my homework on the road.
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  • While I was able to log in and complete some of my homework, it was bumpy and challenging to concentrate.
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  • So I bailed on the trip. Here are some of the reasons why: School is important to me because I am changing careers in order to earn more and one day be able to retire.
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  • At this point, I'm in sales. and while I previously held jobs where I earned $100K plus, after COVID, I was laid off and lost a few job opportunities due to the fact that I didn't have a degree despite having over 14 years of experience in the different jobs that I applied for.
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  • I'm currently earning what I was making in my 20's. My children are no longer planning on being out of town for the holiday.
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  • Instead, my son that doesn't live in town, will be coming to town that week. His ex-wife (the mother of the children that I was going to meet) will also be there for Thanksgiving.
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  • While this would have been a great opportunity to meet his children and see the dynamics of the relationship he has with his ex, I felt like I would be so stressed about completing my homework and studying for my final exam the following week that I wouldn't really be able to relax and enjoy our time.
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  • We would have been driving for 4 days total round trip to spend two days in Colorado.
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  • He has a good job and a retirement and pension from his work and he plans on retiring in 6 years.
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  • I'm still struggling at my job and am no where near being able to retire. He has already asked me if I would sign a pre-nuptial agreement if we ever do get married.
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  • I don't have a problem with that at all but it makes it very clear to me that my education for the career change is still extremely important because I will always need to be able to provide for myself and have a plan of my own for retirement.
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  • Thanksgiving week is also the week that my father passed away. This year will mark 5 years since he passed.
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  • It's still very emotional for me. Oh, did I mention that he is still legally married although he had been separated from his wife for over 4 years before I met him and his wife just filed for divorce a few weeks ago.
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  • Am I being selfish for cancelling or is it okay to be my needs first at this point in the relationship?
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Dating-Relationships first date Colorado california Nevada advice We Are Dating red flags red flag first dates retirement online dating dating
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