My best friend Jenny (22) has been dating Tyler (27) for three months and prior to that they’ve been friends for 2 years. I don’t think this man is right for her. Reasons being that my friend is set to graduate this year debt free, has a decent job lined up, car will be paid off this year also (a year and a half after she purchased it), and has decent savings from what she’s told me. Her boyfriend on the other hand seems to be in disarray. No savings, no degree or profitable profession, and a low debt of 5k which isn’t bad. He does have plans of attending college to get a cyber security degree which I think is great. But I have some concerns about their relationships. The biggest red flags:
- First date he brought up wanting marriage.
- Sometimes he would Invite her somewhere and ask her to pay as the bill arrives.
- He wanted to move out and get a place with her after a couple of months of dating and did not have enough money to cover first month’s rent or the application fee. Jenny being generous, paid half even though she was unsure about moving in with him at the time. He did buy most of the items to move in afterwards.
- Texts her throughout the day at work and attempts to call her most days after work. Jenny says she usually doesn’t pick up because she likes alone time after work and she has to study. He seemed to pick up on that.
- Tyler seems irresponsible with his finances. His debts aren’t crazy but I’d imagine someone who is struggling would not have a $700 car note and also feel determined to move out while barely scraping by living under the same roof as his parent.
- Tyler also wanted to arrange a plan where him and Jenny move in together and Jenny pays one utility bill and other small expenses until she finishes college. When she transitions to her new job she will then pick up most of the expenses and support Tyler through his academic journey. I don’t oppose this idea but I’m not a fan due to several factors. Why should Jenny have to acquire and pay for debts that aren’t hers? Why does he need this much support at his age?
Tyler seems like a nice guy but clueless. His financial situation does not help. He takes Jenny on dates and buy her gifts when he can but it does not seem sufficient. I’m not saying he has to be rich or extremely generous, he just has to meet Jenny halfway. My friend is able to save up because she lives at home and her parents support her. She pays no bills except her car note, insurance, and other personal expenses. This kind of arrangement is common in our culture. Tyler on the other hand has always had bills and I understand the circumstances are different. I’ve met Tyler on multiple occasions and I genuinely believe he has limited dating experience and does not see how his behavior is off putting to those who surround Jenny. Most of us were not thrilled to learn Jenny paid half of first month’s expenses for the studio while a close relative of Tyler called Jenny a keeper.
Jenny seems to be noticing things and is starting to get frustrated. I’m unsure of what to tell her. I love her and I know she has feelings for her boyfriend but I also don’t want to ruin her relationship. What should I tell her without overly influencing her decisions in her relationship?
Things I Forgot to mention: Jenny did not move in with her boyfriend. She said something along the lines of not thinking it would benefit her to move into a shared studio while she has her own bedroom rent free. We also live in a city that’s high in costs.
Comments
You don’t need to “tell” her anything. Just listen and let her know you support her no matter what she decides to do
Sounds like you4 friend is seeing the red flags as well.
Tell Jenny the truth about how you feel. Even if the gender roles were reversed this is not a healthy dynamic by any means.
It’s 2025. Men need to seriously step it the f*** up. If they’re not going to school to educate themselves they need to do some kind of training to make themselves professionally stable and therefore on equal footing with the women they want. This society does a huge disservice to its boys by coddling them and telling them that women should be doing everything for them. Time to raise more well rounded individuals regardless of gender.
You can express your concerns and I’m sure her parents are too. Hopefully, she’ll hold off on marriage because in time, if she’s intelligent, she’ll see it. You can also expose her to other couples who have a more balanced and healthy relationship. Maybe they can double date and see it.
Mind your own business. Jenny is taken care of by her parents so yea she’s going to have savings and no bills. You just seem angry that Tyler doesn’t have money.
I’ve been through this and if you want to keep your friendship in a good place, you need to accept that she is an adult and responsible for the repercussions of her decisions. If she is feeling unsure or wants advice she will ask you. And even then, you absolutely cannot expect for your thoughts or insights to result in her leaving him. Otherwise, she will start to resent you and distance herself from you because she will feel she is disappointing you and has to choose her relationship over a friend. It just never turns out well unless she comes to a place within her own mind and heart that she wants the relationship to be over. I had a friend who was with a man who physically assaulted her and saw marks on her neck. Eventually she got upset with me for not supporting her in her relationship and we stopped being friends for 10 years. I thought of her and missed her terribly during that time. We recently reconnected and she’s still with him, they have a 4 year old child now, and he’s still a POS.
You don’t have to say anything specifically about him. Just keep uplifting her and telling her she deserves the best. She’ll make her own decisions, just be a loving supportive friend. Try to let this go, it’s her path not yours. Just walk with her as long as it benefits both of you.
He has a vast multitude of red flags that would cajole all of us to run for the hills. He has his red flags on show for the world to see. He’s broke, no degree, no profession, little ambition, pushy and needy etc etc
And yet your friend still wants to date him. He is not the problem, your friend is the problem for wanting to date someone with a gazillion red flags and you are the problem for not seeing that she is the problem.
Don’t tell her let her tell you and back her up. My best friend is with a complete jerk her daughter told me I had to tell her mom to leave. I can’t do that people leave when they are ready and not until. If I told her what to do she wouldn’t be my friend for long. Unlike your friend if she leaves she leaves with nothing but the clothes on her back. We live next to each other so her moving in is only if she has to leave. Her choice I’ve told her she’s welcome.
Some people are terrible at choosing romantic partners. Jenny may be one of those people. She may make terrible mistakes. However, it’s almost a universal truth that people don’t like being told that they are fools, even when they are. Unless Jenny asks for advice, she doesn’t want it, even if she needs it.
You have to decide how much you need Jenny, and whether you are willing to risk ending the friendship over her poor choices. Maybe she will see the light and dump the loser. Maybe you can push her in that direction. But the more you push, the greater the risk she will side with him.
“There are several red flags with Tyler that I don’t think you should ignore.”
If you tell her that he’s not right for her she’s just going to resent you. You have to be more subtle about leading her to come to her own conclusion that they are just on two different levels.
Ask her questions like how long do you think it’s gonna take Tyler to finish school? Is he gonna go full time? Sounds like a long time how old will he be before he gets a good job? Are you gonna be able to financially support him while he’s in school? Ask her if she’s ever gonna want kids and remind her she has a biological clock. (women have a limited amt of eggs and age is a factor) Ask her things along those lines so she’ll see the light.
Ask if she allows her emotions to make her relationship decisions? The answer is yes even if she won’t admit it. Ask her to think about some of these decisions logically. Let her come to the conclusion that he’s not the right guy for her.
Good luck!
Jenny sounds like a smart girl and you sound like a great friend. I hear that you are concerned about your friend. All you can do is tell Jenny how you feel and what you have noticed. Let her know it upsets you but don’t bring it up too often. In the end, Jenny will make her own decisions. Sounds like she has a good head on her shoulders
Frankly, you only told us bad things about this dude with no context, also, as others already mentioned, she has her parents taking care of her hence the money.
Hopefully, your friend is mature enough to make her own decisions, and yep, you’re being a good friend taking care of her, that’s undeniable.
This guy’s a red flag. One thing I’ll say is I notice alot of women in the future say they regret the past decisions. Stds, becoming a single mother, marrying the wrong man. Well right now she’s in the position to not make those mistakes. Better now than never.
Just tell her to keep being careful, as nice as he may be she sounds like someone who works hard for stability in her life, and it sounds like that guys approach to finances is playing Russian Roulette with 5 chambers loaded with “spend money first, worry never” bullets. They don’t sound very compatible