“Which Guy Should I Choose?”

I have been in a relationship for a year and a half now. I believe I have never loved anyone like I have my boyfriend, and he’s great to me. For just over a year he has stopped doing things with me though and stays home leaving me to hang out with my girlfriends, which bothers me. So in the meantime and not on purpose, I have made friends with a guy who has a solid career at his father’s business. He has promised me that if we were together, he would provide for me and treat me better than I’m treated in my current relationship. I would be able to go home and see my family, who lives 1700 miles away, a lot more than I do now. I could even go home in the summer and spend a couple months on the family farm. I would also be able to quit my very fast-paced government job and work at his father’s business. All of this sounds amazing to me, of course. The business he has is something I have always dreamed of working at. So do I throw away my current relationship, with someone who I feel is my best friend, for a different lifestyle? What if this other guy and I don’t get along as well as my current boyfriend and I do? What if I spend my whole life wishing I had picked my current boyfriend? Or what if I will be happier than I am now? — Undecided

What if, instead of relying on guys to provide your lifestyle and enable you to visit your family and do work you’ve dreamed of doing, you pursue these things on your own, yourself, like a grownup? What if, instead of basing your decision to pursue relationships on what a guy can provide you and do for you, you get to know people who spark your interest and pursue relationships with them based on: mutual respect and admiration; shared values; common interests; compatibility; chemistry and passion; the way they make you feel? All of this sounds amazing to me, of course. I would hope it would to you, too. But if it doesn’t, I’m afraid the best advice I can give is a common refrain here around DW: “If the question is which one? The answer is neither.”

I have met a great lady and need some advice. We are both 43. She has been married two times, and I have not. She has three kids out of the house whom she helps with college. I have a dog. We both have great jobs. I own a restaurant and she sells me my food. She makes about $60,000 more than I do. She is very religious and I have just started attending church with her in the past four months. We have been together about eight months. One problem is if I miss church, she gives me the silent treatment for a day and acts very disappointed. (But it’s ok for her to go out of town for the weekend and miss.) I have a job that requires my time on Sunday sometimes. I feel like she should be happy that I’m going to church more now than I ever have. My other problem is that I won a trip to Vegas through a pool tournament. Well, she wants to go and asked if she could. I said, “Sure, get yourself a ticket.” She said, “Well, are you going to pay half? You didn’t even offer.” I said, “Do you need me to?” Well, I was extremely frustrated by her expecting me to pay for it. I pay for about 99 percent of all dates, dinners, movies, trips, and entertainment in our relationship. I have bought her tires. We also went to Vegas about a month into our relationship. She paid for her plane ticket while I paid for everything in Vegas including two high-priced shows. She brings up traditional values and Biblical roles of the man and woman. I am traditional in many ways but also value a team effort in many aspects of a relationship. I told her it would be nice for her to pick up a tab every once in a while. She doesn’t seem to budge much and says she has college tuition and other stuff to pay for — like she gets to save money and I don’t! My money is our money and her money is hers. Please help me with any advice. — Biblical Roles Aren’t My Jam

I guess we know why she’s been divorced twice by her early 40s. Not only is she stingy, but she’s also demanding and high-maintenance to boot. You two may simply have values that differ too much — like you value not running out of money and she values having everything paid for. And you value being accountable to your work, while she values your dropping everything to go to church with her every week (or every week that she goes). I don’t know why you’re putting up with her shit, to be honest. You didn’t say one good thing about her or your relationship. She gives you the silent treatment for a day if you miss church? She’s 43 years old, has grown kids, and gives you the silent treatment? She has not learned from her two failed marriages. This won’t end well. MOA.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Avatar photo Cleopatra Jones says:

    Nailed it again, Wendy.

  2. ele4phant says:

    LW – if faced between choosing between two guys, the answer is always none of the guys.

    Also – if you don’t like your lifestyle and job, change it on your own. You don’t need a boyfriend to do that for you. Quit that job if you hate it. Move back to your family farm if you want.

  3. LW1: Let’s pretend your question is valid at all because Wendy hit the nail on the head. You know new guy as a friend. You have ZERO idea how your actual relationship would play out and yet you are already willing to go into it working with him and revolving your whole life around him and this possible scenario. That makes no sense. Work on your current relationship or MOA if it isn’t working for you. Even if you decide to date the friend you shouldn’t be working with him and completely changing your life for him overnight.

    LW2: Ya she seems like a pain. Even if she had just phrased it “i would love to go but I would need some help with the plane ticket if you could?” it would have sounded better. I agree with a lot of traditional gender roles, just how I was raised but like you said it still has to be a team effort. If she really cared about you, once you brought up her picking up the tab sometimes, she would at the least grab a cheaper meal now and then or something. My ex made A TON more money than me and I still would bring over groceries, make elaborate meals since he loved my cooking, grabbed some of the smaller checks now and then.

  4. Ugh the skeaziness of that line, I will treat you so much better, I can’t even. Know that that guy is just blowing smoke up your ass. He sees how vulnerable (and maybe not smart?) you are and sees a fun conquest. I just cannot ascribe good motives to that guy.

    1. dinoceros says:

      Yeah, anybody who spends actual time trying to convince someone to dump their current partner with an actual list of reasons is pretty douchey. And saying words doesn’t make them true. Sounds like he realizes that the LW can be persuaded by $$$ and is trying capitalize on it.

  5. dinoceros says:

    LW1: Have you ever heard the phrase “if you can’t choose between two guys, choose neither?” You have to make your decisions about each of them separately. You list a bunch of stuff that would change in your life with the second guy that has nothing to do with him. Is there anything you like about him besides his business and finances? With your current boyfriend, you say he doesn’t hang out with you anymore. Have you talked about this? What does he say?

    1. dinoceros says:

      LW2: Move on from this lady. Her view of relationships (man pays for everything. Woman scolds man like she’s his mom) is not what you’re looking for. She’s not going to get any better. This is who she is.

  6. LW1- if the friend’s family business is something you “have always dreamed of working at”, why not make the case to work there? if you have skills, background that would make employment a good fit, then use that as a network to go for it. But do it without the expectation that you will use it as a springboard to a relationship.

  7. bittergaymark says:

    LW1) Eh, go for the rich guy. Uf it falls apart, so what? The current guy sounds dreary as fuck. That relationship has run its course. MOA.

    LW2) Tell her it’s been fun… but now, you can see things / for what they / really are / you know / it’s not that far / you’re at the point of no return… whoops! Sorry, starting slipping into some obscure Madonna lyrics… Where was I again? Oh yeah, tell her that now that you know the truth, eh, it’s pretty much time for her and her fucking church to go fuck off.

  8. LW1: Since you mention no romantic relationship with the new guy, and not even the slightest romantic interest, this sounds like a business arrangement. Is that what you’re looking for? A sugar daddy? You provide sex and companionship, he pays your living expenses and travel costs?

    1. bittergaymark says:

      I don’t think this is exactly fair. They aren’t together yet romantically as she is involved with someone else, duh. And as far as comparing this guy financially to the other guy, come on. Quoting Marilyn Monroe in Gentlemen Prefer Blondes — “Don’t you know that a man being rich is like a girl being pretty. You wouldn’t necessarily marry a girl because she’s pretty, but My Goodness! Doesn’t it help?”

      1. I didn’t mean any insult by saying it sounded like a business arrangement: if it works for them, it’s perfectly fine. It just struck me that she said she’s never loved anyone like guy #1, but the only thing she mentions about guy #2 is what he can provide financially. She said she doesn’t even know how well they’d get along, which implies that they don’t know each other very well.

        It’s just sort of a backwards approach to relationships – usually there’s some romantic connection, before a guy starts talking about supporting you and paying for your travel. That he’s framing this as “if you date me, I’ll support you, give you a job and pay for trips” right out of the gate makes sound like he’s offering an “arrangement,” to use the old-fashioned term.

  9. Hypocritese says:

    Biblical values yet she is divorced twice ……..

    1. artsygirl says:

      I wonder if she is also against gay marriage because it “destroys the sanctity of marriage”

  10. Juliecatharine says:

    Both these women sound like sugar baby wannabes to put it nicely. LW2–dump her, hard, and have fun in Vegas where at least the hookers are honest about what they are.

    1. LW #2 doesn’t sound like a sugar baby. She’s not young and she is making big $$ on her own, with no indication she plans to stop working. She sounds like someone who believes a man is required to pay all dating expenses and if he marries to fully support his wife, while anything she earns is hers, even if she earns 50% more than him and he is left with no spare cash after supporting her in the style to which she has or wishes to become accustomed. In her case she’ll likely treat herself to extra luxuries and pass on $$$ to her adult children. Not the sort of woman I would advise a guy to date or marry, but not a sugar baby, either.

  11. Avatar photo Moneypenny says:

    Regarding LW 1- it sounds a bit to me like she’s fantasizing about this great life she thinks she would have with guy #2 because it makes it easier to deal with what she’s not getting out of her current life with guy #1. It’s a way of coping, in a way, with her current reality.

  12. artsygirl says:

    LW1: I am not even going to address your current relationship because only you can determine if it is over. To my thinking, never trust a man that promises you the moon because he is likely taking you for a ride. Not only is he guaranteeing you a position in his father’s company (does he have the power to hire people?), but he is also promising to support you for three months while you visit you family – would this be before you start this new dream job or after? I can’t imagine a new employee being granted a multiple month vacation right after they start a new position. Also, what happens if the relationship does not work out? Are you going to lose your new dream job? Would you be working under your new boyfriend, because there are countless instances where that would be considered a huge conflict of interest and likely cause issues with HR – and since he is the boss’s son and your are a new hire, guess who automatically is booted out of the company if there are complaints of interoffice fraternization.

    LW2: Your GF sounds like a bloody hypocrite that insists you follow arbitrary standards of behavior that she doesn’t even bother to hold herself to. Dump her, have a great time in Vegas, and hopefully find a new food vendor.

  13. IsabelaCaroline says:

    Dear Undecided,
    I think you should stay with your current boyfriend. As you have already said, you love him and love him for what he wants. Also, you’re already together for a long period of time so it isn’t right you exchange it for someone you have just met.
    If he dosn’t treat you as well as before, try to talk to him to find out if something is wrong, dialogue is central to your relationship. Your relationship may just have fallen into the rut. If the problem is this, try to cheer him up, surprise him and convince him to leave because after all, you’re his girlfriend and he should be dating you.
    If that doesn’t work, get him to fight for you. Take time out of whatsapp, facebook, twitter or any other social network that he also has, don’t go to his house for a while, don’t ever go out with him, focus on you. In this way he’ll realize that something is wrong with the relationship, you’ll feel how bad your absence is and you‘ll see that you don’t deserve what he’s doing to you and then he’ll take some action to change that. This way, it’ll value you as you deserve, because you can’t try to save the relationship alone.
    If he doesn’t miss you, it means that his love for him isn’t reciprocal and that the solution is to really take time for himself and to value himself more.
    As for the well-resolved man who has a solid career in his father’s business as his friend, he should help you see your family and try to get the job of your dreams. If he really likes you, it’s not fair that he just makes you feel good if you have something else with him.

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