Dear Wendy
Dear Wendy

“I Message Women On Craigslist. How Can I Make it Up to My Fiancée?”

Three letters today:

I’m 30 and my fiancée, “Jill,” is 32 and we’ve been together almost four years. She works during days and I work in the family business. Sometimes I go on Craigslist and message women and talk with them, saying dirty things, but I have never wanted to meet them. It’s, like, the communication that intrigues me, I guess. Sex, which is only about three times a month, is always planned and revolves around her. It can’t be spontaneous; I can’t show her affection without her saying I’m “too over-bearing” when all I want are some hugs and kisses. I don’t think that is over-bearing. I love her and her body, and I just don’t understand why I feel like I have to message other women. I don’t have many friends; I work a lot. She does everything with me. I don’t have much guy time and, if I do, she’s mad at something for some reason. I love her and I don’t want to lose her. She looked at my email and saw a handful of emails with other women and told me to figure myself out and that she was already over it. I do want to figure myself out. In the meantime, how can I make it up to her and explain it so she understands that I’m stupid and I don’t know what I was thinking? — Stupid

Why are you engaged when your relationship is in so much trouble? Your communication stinks, your sex life is one-sided, you’re lonely and sound depressed, and you put much of the blame on your fiancée’s dismissiveness of you. You want to figure yourself out? Great. Make an appointment with a therapist. Break up with your girlfriend — or, at the very least, put your engagement on hold — so you have the time and energy and focus to devote to yourself. What you’ve described does not sound like a good, solid, happy relationship. It sounds like a (co-dependent) relationship that has run its course and needs to end. You mention that Jill works during the days and in the next sentence you say that you find women on Craigslist to talk dirty to and that the communication intrigues you. You think Jill’s working has something to do with your seeking out other women? It does not. Jill’s disinterest in you and complete disregard for you and your needs sure might though.

So, start there. Do some soul-searching — on your own and with the help of a professional — to figure out why you’ve agreed to marry someone who doesn’t seem to care about your needs and doesn’t really want you to touch her. Do you think this is what you deserve? Did you lack a model of what a healthy, happy relationship looks like? Do you think you can’t find anyone else? Do you truly believe you’re stupid? For the record, you don’t sound stupid to me. You sounds incredibly lonely and sad. I don’t think Jill is helping your cause at all. I’d say “girl, bye” to Jill until you “figure yourself out” and, dude, make some friends. Something tells me that, when you do, you won’t want Jill after all.

I met my boyfriend in mid-November. I’m about to turn 45 and, at this point in my life, I know what I want and what I am looking for. To make a long story short, we were looking at rings two weeks ago to get engaged, and he ended up buying the ring two days after. We were both very excited about taking the next step in our relationship. Was it quick?! Yes!! But we both felt like we were soulmates. I honestly have never meet anyone like him before. However, we ended up getting into a heated argument, and I said maybe we need to wait a little bit more time to get to know each other. Without a second thought, he returned the ring. This was literally our first fight. He’s also been burnt in the past from more than one woman. He ended up buying a new car, and he used the money from my ring for a deposit. I am now pondering whether this man truly loves me, if over one argument he could just return the ring for a new car. Don’t you think if he was “in love” with me, he would have kept the ring until we were both ready?? Why do you think he jumped the gun so quickly? — Thought I Was Ready

Sounds like you both had some reservations about moving so quickly — that you realized on some level you didn’t really know each other very well and that then, when you had that fight, it gave you both an opportunity to back out of what you weren’t ready for. That’s why you said you might need to wait a little bit and get to know each other, and why he immediately returned the engagement ring. You both knew on some level that getting engaged right now didn’t feel right. And it sounds like, by using the money for the engagement ring to buy a car, your boyfriend went a step further in ensuring there wouldn’t be a proposal — or at least, not as much money for an engagement ring — for a while. That’s why he “jumped the gun.” It was a clear message to you and the message is: I’m not ready for this either. Slow down, get to know each other, and pay attention to the other messages he has for you before you even think about committing your life to this guy. (P.S. Here are 15 things every couple MUST discuss before getting married. I have a feeling there may be a few things on the list you have yet to talk about with your boyfriend.)

I moved cross-country to be with a very special man whom I love very deeply. Almost two years in, I got pregnant and we now have a beautiful baby. He also has a child from a previous marriage who lives three hours away, which is why I was the one who moved. Ever since I arrived, it has been one struggle after another. I was employed and lost my job after my employer found out I was pregnant. I have been unemployed since our baby was born. I’m grateful I’ve had over a year with our baby, but we’re really strapped for cash and I haven’t been able to find work (and I’ve tried everything!). Here’s the kicker: I hate the state we live in. I want to go back home, but I struggle with talking to him about it. I just don’t know how to approach the conversation. He is extremely sensitive and, even though his controlling ex-wife has us limited to seeing my stepson (we’re lucky if we see him on one weekend a month during the school year), I don’t think he would agree to moving away. Plus, he hates change. I don’t want to hurt his feelings, but I feel like I need to let him know how I feel. — Hate This State

Don’t frame your conversation around your wanting to move. Instead, frame it around the real issue here: that you’re unhappy — maybe even miserable. Why are you unhappy? You say you hate the state you live in. Why? Can you list three to five reasons that you hate it? If you can name the reasons and share those with your partner, then the two of you can discuss together how you might better deal with those things. I’m betting, with the possible exception of weather, that most of the factors in your unhappiness are addressable (here’s a guide to finding happiness that may help you). Unemployment, loneliness, and feeling isolated, for example, are all things that you — and your husband! — can work on. And if you literally cannot make your situation better enough to be happy, then the two of you have to decide together whether there’s another place — which may or may not be where you moved from — where you can all find employment and stability, and still maintain regular visits with your stepson.


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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].

20 comments… add one
  • artsygirl January 26, 2017, 10:28 am

    LW1- I think a part of you wanted to get caught by your fiancee after all you kept illicit messages from other women! It sounds like you and your fiancee have different needs and I doubt if you will be able to fix them. You are a physically affectionate person and your fiancee is not, you want sex more often and she does not – these are huge red flags in the relationship. Don’t think that marriage is going to fix these. Follow Wendy’s advice please.

    LW2 – You and your BF have been together less than three months so slowing down the relationship is the prudent thing. Also, did you BF need a new car? Does it make sense that he uses available funds rather than holding onto a ring for an engagement that might not happen for months or even years?

    LW3 – It is great that your partner wants to have an active role in his child’s life. Since he is already three hours away from his son, do you think you could compromise and find another town or city to live in that is approximately the same distance? That way you have a say in the home and community and hopefully would have more luck finding employment. Also, have you spoken to a lawyer regarding your termination? It is illegal (at least right now) to fire an employee simply because she is pregnant.

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    • carolann January 26, 2017, 3:40 pm

      It is very difficult to prove you were fired because of pregnancy. It actually happens a lot. It happened to me many years ago when I worked for a major corporation. I had been there nearly two years. I had just received a sparkling review only a few months before. I made the mistake of telling a female coworker before I officially notified my boss. I was almost instantly let go. They claimed it was poor performance, but of course, it wasn’t. My performance didn’t suddenly change!
      Because of the nature of my position (I handled very sensitive information) it would have been difficult to have someone temp for me while taking leave. I understand their reasoning for doing it, but they “did me dirty”! Lawyers are expensive and the legal process can be very drawn out. You have to be able to prove pregnancy was the only reason they had to fire you. In my case they claimed they didn’t even know yet. Of course, I know they did!
      I didn’t have the money or energy to fight it and it would have been a long shot to win.
      I learned my lesson…don’t EVER tell a coworker anything before you notify HR.
      I did receive full unemployment. BTW, the coworker ended up with my job, but because the company lost a large automotive contract (with the largest car maker in America) she got laid off a few months later.

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  • Northern Star January 26, 2017, 10:53 am

    LW 1: You’re cheating on your fiancee when you message randos on Craigslist. You know that, right? And yet you keep doing it—clearly your relationship isn’t giving you what you need. End it honorably instead of getting your jollies online behind her back.

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    Bittergaymark January 26, 2017, 10:57 am

    LW1) You act out so because you are engaged to a non-responsive, boring, sexual dud in bed. You are NOT a match. MOA.
    LW2). You are so not ready to get married to this stranger. Bravo to him for using the ring money for something far more practical and actually useful.
    LW3). Ugh. Expecting a man to move away from his child is typical horrible second wife / baby mama behavior. Frankly, its unbecoming. Don’t want to be the typical brat? Then don’t.

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    • Ron January 26, 2017, 12:42 pm

      You are totally correct about LW1. If sex is infrequent, nonspontaneous, and less than thrilling after only 4 years together, marriage won’t improve things in the least. Beyond that, this woman is controlling. LW needs to dump her and MOA. He may ‘love’ her, but he’ll never be happy with her. I have a family member who married women like this. It never got better. It was a living hell until he was old enough not to really care about sex or even hugs and kisses anymore, but it was a terribly sad thing to watch. He ‘loved’ her, so he stayed. I think he was mainly afraid of loneliness, but could have easily done so much better.

      Also totally right on LW2. Immediate chemistry is not the same as ready to marry. This woman has a lot of nerve — after they decided together to get engaged and buy a ring together, she announces she isn’t ready yet, and then blames him for returning the ring. Most stores have a limited return policy on rings and if he just sticks it in a drawer, he won’t be able to ever get back the money he spent — it’s like how a car loses value the moment after you drive it off the lot.

      Three for three, also agree with you on #3. It is very unclear that a move back to her original state will be the happiness panacea this LW expects it to be. Also, she has a legal case if she was fired because her employer learned she was pregnant. That’s been illegal for a long time. The public hates that sort of thing also, so just the shame of the lawsuit will hurt this guy’s business and he’ll cave, especially since the law is totally against him.

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        Bittergaymark January 26, 2017, 3:23 pm

        The return policy issue is an excellant point…

  • SpaceySteph January 26, 2017, 11:21 am

    It’s weird to me that you say you hate the “state” you live in. My guess is that you are buying into the state’s reputation without having actually given it a chance. Of course you hate a place where you are isolated and unemployed. But that’s not really about the state.
    States are rarely homogeneous– a bigger city or a smaller town could have a totally different vibe from the place you live now while still being in the same state or region. . I live in Texas and grew up in Florida and those places both (are)/(are totally not) exactly like you’ve heard… depending on which part you’re in. Even (gasp) Mississippi, has redeeming parts.
    You are stuck within a small-ish radius from where you live, maybe within the state or maybe you can move to the edge of a neighboring state, but you’re not moving cross-country if you want your bf to have a relationship with both of his children, so stop thinking about it as “I hate this whole terrible state” and start looking for and embracing your state’s redeeming qualities.

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  • Janelle January 26, 2017, 11:37 am

    LW2: Mid November, that is barely 2 months. You surely couldn’t think something wouldn’t come up that could slow this down. You barely know someone is 2 months, heck 2 years sometimes. This sounds like a good opportunity to slow down, get to know each other. You can be just as committed and in love without an engagement.

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  • baccalieu January 26, 2017, 12:29 pm

    LW1, Wendy gave you a very sympathetic response, and she is absolutely right. You are not (low level) cheating because you are stupid, you are doing it because you are unhappy. How is this relationship working for you and how does this woman take into consideration your needs? It certainly seems like she doesn’t do so at all with respect to physical contact and intimacy. If she doesn’t do so in any other area, then she is not the right person for you. It also doesn’t seem that she cares that much about you if her reaction to you talking sex with other women is “I’m over it.”

    And really, LW2, YOU suggest after a fight that you ought to slow down (which is a damn good idea in my opinion and just about everyone else reading this) and because he agrees too easily you conclude that he doesn’t love you. Who gets upset when their partner agrees with them? Apparently, you didn’t mean your suggestion that you slow things down and simply intended to provoke him into saying, “Oh no, no. Please don’t do that. I couldn’t bear waiting longer to marry you. I am sorry I argued with you and next time I will agree to whatever you want. Just don’t suggest we should delay the engagement.” Grow up!

    You two were rushing into an engagement way too quickly and all that has happened is that you’ve come to your senses. At least he’s come to his senses, you were only pretending to come to your senses in order to play games with him. Try to recognize that his new attitude is the sensible. (BTW it does occur to me that his spending the ring money on a car is his way playing games with you, too: “Oh now, you’re not sure you want to get married. Well, I’ll show you how little it matters to me. I’ll spend the ring money on a new car. How do you like that?” If this is the case then it is even more important that you not get married as neither of you is mature enough to do so.).

    LW3 – WEES

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  • for_cutie January 26, 2017, 12:46 pm

    LW1: MOA.
    LW2: MOA.
    LW3: Talk to your husband (is he your husband, you didn’t say?) Maybe you need to lower your expectations for work. My friend was a retail store manager, and after she had kids she worked as an evening check out person at Target. She didn’t love moving backwards professionally, but it got her out of the house, making a living, making new friends with coworkers, and her husband stepped up with the kids. Just a thought.

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  • Ron January 26, 2017, 12:48 pm

    I don’t think LW2’s bf is playing games with her. When you buy a ring together and are then told ‘on second thought I’m not ready for this yet’, there is a very big chance that she is never going to be ready and that the relationship doesn’t have a long life. Bf would be very stupid to just keep the ring in a drawer, thus tying up all his available capital, in the likely vain hope that she wishes to marry him in 6 months. I agree both of them really rushed this and that they likely both dodged a bullet here.

    I think there may be a little greedy going on here in LW’s thinking. She already sees the ring as her property. It isn’t.

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    • RedRoverRedRover January 26, 2017, 1:17 pm

      Yes, I think it was totally reasonable to return the ring. Like you say, it probably had a return policy where he could get his money back. Later, he wouldn’t be able to. He’d probably lose half the money if they ended up not getting married.

      As to the car, I’m sure he was feeling pretty bad after she broke off the engagement. And he suddenly had a chunk of cash freed up. No big surprise he went out and got himself a consolation prize. Was he trying to get back at her? Maybe. But maybe he was just trying to cheer himself up.

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      • artsygirl January 26, 2017, 2:03 pm

        It is likely the money was originally saved for a car since they have only been dating since November. After all, very few people have enough money for an engagement ring or car just hanging out in their bank accounts. Since they decided not to get engaged so quickly, the BF very reasonably made the decision to use the funds.

      • SpaceySteph January 26, 2017, 2:36 pm

        Alternately, dude is an impulse spender of thousands of dollars (why buy the ring in the first place?)… which the LW might know if she’d been dating the dude longer that a couple months!

      • RedRoverRedRover January 26, 2017, 3:04 pm

        Like for me, if I was going to make a big purchase like an engagement ring and I didn’t want to go into debt to do it, I’d sell some investments. Then if I got the money back by returning the ring, I’d have that chunk of money sitting there… either to put back into investments, or to do something else with. If I’d been thinking I needed a new car for awhile, it would make sense to just use it for that since it’s already cashed out.

        But yeah, getting the ring in the first place after 2 months is a bit crazy.

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      Bittergaymark January 26, 2017, 5:35 pm

      I agree. I think returning the ring was the ONLY sensible reaction. Remember, everyone, this is a two month long relationship. To get married at this point is statistically unwise to say the least…

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  • Gwyneth6 January 26, 2017, 3:32 pm

    Oops- what I was meaning to say is LW3 don’t move till you get custody sorted. Your stepsons mom should not be holding him away from his dad. After that’s set you could consider a 3hr radius from your stepson town. Or maybe further if custody is something like you guys have your step son for extended vacations on his school breaks but not monthly. Consider both of your future earnings. Take some little road trips to check out areas while you’re sorting out custody.

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  • dinoceros January 26, 2017, 6:18 pm

    LW1: You can tell her, but she’s probably not going to believe you. Surely you understand why. But I agree with Wendy — why are you engaged? Marrying someone whose sex habits drive you to message other women is a ridiculously bad idea. Have you ever talked to her about your sex life? I don’t think this relationship is going to end well.

    LW2: You’re using the fact that you are older as an excuse as to why it wasn’t incredibly naive and careless to get engaged to a man you barely knew. You’re upset that he took the ring back after your first fight. WHY THE HECK are you engaged to someone you’d never had even your first fight with? I think it’s important to understand that age doesn’t make feeling like soulmates is more substantial than feeling it at age 16. Sure, you know what you want, but you have to use that information logically. It doesn’t mean that you’ll suddenly only feel in love with someone if it’s a good idea.

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    • dinoceros January 26, 2017, 6:24 pm

      LW3: I think that it’s a valid conversation, but you need to manage your expectations. When you say move “away,” what does that mean? Certainly you probably know that it’s unlikely (and bad parenting) to move further away from his son. But as someone mentioned above, there still should be a variety of options of other types of towns/cities or even states in a similar radius. But you do need to figure out what you don’t like about that state so that you can make a reasoned decision on what options would actually be good. However, I think it’s not the best idea to move to someone because of their child and then expect that you can move away later. That’s one of the reasons I don’t date people with kids.

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    meadowphoenix January 27, 2017, 1:17 pm

    LW1: Have you even had a conversation about your differing sex drives and the fact that she doesn’t want to be touched? Because the relationship should be focused on both your needs, and you should be able to say what’s non-negotiable to you both (and break-up if those non-negotiables are too far apart) And unlike Wendy, I do think you’re a little emotionally stunted if you genuinely don’t know why not being able to touch your girlfriend and being resentful of the sex you do have would make you want something reciprocal from somebody else. But I also think you genuinely do know why and you wrote in here to get sympathy, just like you wrote to those women to get validation. Find someone who likes you the way you want to be liked.

    LW2: Honestly, you guys do need to get to know each other. And you need to shit or get off the pot: either you really wanted to slow things down, in which case the return makes practical sense (although again if y’all had good communication, he would have told you that what he was going to do, and you could talk about how you’re going to get to know each other), or you were playing games and tough luck someone took you seriously. But good lord, the fact that you probably don’t even know if he wanted a car or not suggest volumes about your ignorance of him.

    LW3: Find out if you have a legal case or if you would like to pursue it (I think you waited too late to file an EEOC complaint, but that would have been the less expensive route). Find some friends, go to meet-ups, try to develop a life in this town away from your husband, then think about your hatred. Get your boyfriend to get a custody agreement, courts do not look fondly on parents who limit access of children unilaterally. Look very carefully at your career. Where can you find good jobs for it? Is there an adjacent career that has a lot of openings in the state your in?

    What I’m saying is that the best way to head off sensitive feelings is to be clear about your feelings and clear about solutions. Do not let him minimize your feelings; do ask him to find solutions with you. Try those solutions out, even if you don’t think they will work. Avoiding sensitive feelings isn’t going to help your marriage, but honest communication will.

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