“My Best Friend Wants to Cheat on her Fiancé”

I’ve been close with my best friend for about four to five years now — since high school — and about a year and a half ago she got engaged. She’s 20 and her fiancé is a 46-year-old man and her former teacher. Although I don’t agree with her getting married so young and to someone who could pass as her father, I’ve refrained from saying anything harsh or discouraging about their relationship since he does treat her better than anyone she’s ever been with and she truly seems to be in love with him. But she’s been having doubts since the very beginning, and if anyone ever asks, she says she’s single and not seeing anyone; her reasoning being it’s none of their business. Also, since he is her former high school teacher, she fears he could lose his job if word got around, which I can somewhat understand. She’s even agreed to go out with exes for lunch dates, and talks to them on a semi-daily basis without revealing that she’s planning on getting married in a year.

Recently, she told me she needs a break from her fiancé and wants to see what it would be like to have sex with other guys. I feel as though by not putting my foot down about her going out and talking to these other guys that I am condoning her cheating on her fiancé. I also feel that if I don’t voice how I feel about her making the wrong decision in getting married right now, then I’m willingly letting her make a decision that I think is a bad one. How do I go about being the “good friend” here? It also doesn’t help that I’m to be her Maid of Honor next year, and I feel as though I can’t help with her wedding planning and stand up for her while having these feelings about her getting married. What do I do? — Reluctant Maid of Honor

First of all, let’s get something clear here: you aren’t in a position to “let” or “allow” your friend to do anything. She’s a grownup and she’s your peer. No matter how much you might disagree with her choices, you don’t have the power to “put your foot down” and demand she change her plans or behavior. What you do have some power to do is voice your concern, but keep in mind that you run some risks when you do that. Specifically, you risk alienating your friend if she doesn’t want to hear what you have to say, and at a time when she’ll likely need you the most. But if that’s a risk you’re willing to take, especially if the risk of what may happen if you don’t say something seems bigger, then by all means, speak up, but be smart and strategic in how you go about it.

What you need to make sure you do is frame your conversation around your concern about your friend’s commitment to her decision to marry, not around your opinion of that decision. Be careful that you don’t say her decision is “wrong,” but just that you wonder if she’s absolutely sure about it, and if she is, you’re confused as to why she’d risk that relationship by cheating. And then tell her that if she’s made her decision and she has no plans to change her mind, you’ll support her but you cannot support or condone cheating of any kind.

As for being her Maid of Honor, it may help you to think of it this way: you aren’t necessarily standing up for and supporting the marriage; you’re supporting your friend. One of the best gifts we can give the people we love and care about the most is unconditional support, even — especially, actually — in the face of stupid decisions. Support is not the same as approval. It’s having someone’s back when they’re walking toward something they may not be able to handle on their own. And when is that support more needed than when someone’s walking into a marriage that seems doomed from the start? Be her Maid of Honor; have your friend’s back. If she goes through with her decision to marry, she’s going to need you in her corner, despite how painful it may be for you.

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


  1. ArtsyGirly says:

    LW – are you sure you want to be friends with this girl? She sounds impulsive and not a little immature. There are few things I hate worse than cheating, especially if it is premeditated. I wondered if she didn’t want to change her facebook status and inform people because if she cheats and gets caught then no one will know. The fact that your friend wants to retain her relationship with her fiance but sleep around with her exs is reprehensible.

    Personally if I were in the situation I would talk to your friend. I would also pull myself from the position of MOH because the fact she couldn’t tamp down her hormones enough to be monogamous to her fiance is one strong reason to object.

    Beyond that, I think her relationship is pretty creepy. The guy was her high school teacher? If they had a normal courtship (say year or two) he started dating her right when she turned 18 which means she might have been a senior or a really really recent grad. Pretty pervy in my mind.

    1. ArtsyGirly says:

      umm also she said she wants to know what it is like to ‘have sex with other guys’ does that mean she lost her virginity to her teacher? I have Van Halen’s song “Hot for Teacher” running in my head.

    2. Skyblossom says:

      Totally agree about the pervy. It is completely creepy.

    3. Age differences don’t tend to bother me much provided the younger one is actually old enough or has the head on their shoulders that they can make grown-up decisions (based on the LW’s friends actions I’m leaning toward this not being the case).

      1. ArtsyGirly says:

        I totally agree. One of my friends from college married a guy that was twice her age. They have one of the happiest and most stable marriages I have ever seen. When the groom gave his speech at the wedding he told her that he had been waiting decades for her to show up. There wasn’t a dry eye in the restaurant.

      2. demoiselle says:

        It isn’t the age difference so much as the fact that the older man was her teacher–and only a couple years earlier! … that really is creepy and inappropriate.

    4. Anne (I Go To 11) says:

      This bride-to-be kind of reminds me of Mel on “Flight of the Conchords”…only, Mel admitted she was married, and despite her obsession with the band, she never got very far with Bret and/or Jemaine.

  2. Damn, I wish LW’s friend was the one that wrote in. THAT girl could seriously use some advice. As for LW – Wendy, as usual, you are spot on. I do think she should say SOMETHING to her friend, cause that girl’s about to do something that just sounds bat-shit crazy to me, but proceed with extreme caution and preface everything with the fact that she cares about her and just wants her to be happy.

    1. I thought the exact same thing – i with the friend were the one writing in!

  3. There are a couple ways in which you can approach this situation. You could try and make some financial gain by making wagers with your other friends on how long this marriage will actually last. Side bets can include the method in which they break up: infidelity, growing apart, or Alzheimer’s. You could point out that when she is his age, he’ll be 72. You could also try to get her interested in other men; Hugh Hefner will likely be single again before long.

    Sorry, I think guys and girls have different ways of helping friends. I prefer the ball busting approach.

    But for you, I’ll see if I can put on my “decent human being” hat. If I understand your actual problem with the relationship, as oppose to the one I made up above, then you are worried that she doesn’t really want to be with him and is likely making a pretty bad life decision. This can be concluded through the fact that she denies being in a relationship with him, wants to be with other men, and has had doubts on the whole thing since day one. It sounds like she is just not ready to be in a relationship, let alone marriage. As a friend, you just need to support her. If she asks for your opinion, you can give it to her. But otherwise, just be happy it’s not your situation. People are going to do what they are going to do. Pushing the issue will only push her away. She’ll still end up with him and you’ll be out a friend.

    But on the plus side, I’m sure he will get along great with her parents. They’ll be able to talk about all sorts of things, such as what it was like to grow up in the 60s. Okay, that was the last age joke. I promise.

    1. HAHA i am not a guy and i agree with the straight forward approach to this. this relationship is just soo creepy not only is he old enough to be her father (I am 22 and my mom is 44) but he was her teacher!!! thats just creepy!! I get that you should support your friends but really if you support your friend and she continues to do ridiculous and risky things to her relationship and she confides in you, how can you keep such as secret and still look at your friend in the same way and still actually maintain a friendship? personally i could not handle the situation and i would end up slowly removing myself from the situatio; therefore, i would loose my friend anyways.

      I think its important to take the “ball busting approach” be straight up realistic and even jokey about the relationship. if you have been friends for 4-5 years she should know you have her best interest at heart. i would encourage her to end the relationship instead of cheating is so much worse. i think this chick knows that what she is doing is wrong and she doesnt even fully support her descision to get married this man otherwise y would she be keeping it a secret.

      She jus wants someone to actually voice waht she is thinking which is “what are you crazy??!! how can you marry someone who is #1 so much older, #2 an old teacher #3 you dont actually care about him enough to acknowldge the engagement publicly #4 you are ready to cheat on him” this is messed up!!

      PS: i like the whole making money on this situation with a bet among your friends!!

  4. I certainly agree that the LW should say something. From the perspective of someone who almost married the wrong guy, I was really grateful afterwards for those people who had the courage to (politely) tell me they thought I was making a mistake. However, I am glad Wendy called the LW out for the controlling language she was using (“let,” “put my foot down”). She needs to voice her thoughts and make peace with the status quo, or just remove herself from the situation.

    1. I agree with you – other than the controlling language, if I were in the situation of having a friend telling me that she wants to cheat on her fiance while denying their relationship and all that other crap I would speak up by at least asking a few questions that would get her thinking (like jsw mentioned below about trying to get her to think about the consequences) about why she’s with this guy, why she’s getting married, why she’s actively looking to be with other men, and if she thinks these feelings are just going to disappear after she gets married

  5. The fact that he was likely already teaching – for years – when she was born is a bit creepy. I’ll grant that. Still, presumably they started dating when she was also legally an adult, so, hey, it’s their decision. It’s also utterly irrelevant to the matter at hand. The exact same advice would apply if he were her age or younger.

    I think most of us would also agree that she’s not ready to get married. The red flag is big enough to fly outside of Perkins. There seems to be no sign other than the fact she said yes to indicate that she’s actually interested in marrying him at all. But even so, I’ll give her the benefit of the doubt and assume she truly loves him but started dating him before gaining any other dating experience and wants to live a little before being married. As Wendy said, though, it’s not really the LW’s responsibility regardless, so it doesn’t much matter what the friend is thinking.

    In the end, all that matters is what the LW should do. I agree with Wendy’s advice, and my gut feeling is that nothing the LW will do will have any real effect on the friend’s behavior but might damage the friendship. I believe that, as a friend, when you see someone doing something you feel isn’t a good decision, it’s not your responsibility to stop them, but it is to an extent your duty, as it were, to warn them if you feel they don’t already know the possible consequences. A true friend won’t say “you can’t do that,” but a true friend very well might say “did you think about this consequence?”

    In the case of the LW, I guess all she can probably do is to ask her friend what she would feel if her fiancé found out, because, ultimately, most cheating is uncovered. Everyone wants to think they’re sneaky, but few people actually are that sneaky, especially in this day and age where everything is online. Facebook posts happen. Texts happen. Diseases happen. Coincidental meetings happen. Friends-of-friends happen. If you’re going to cheat, cheat with the assumption that you will be found out. Cheating while assuming you’ll never get caught is like having sex without contraceptives and assuming you’ll never get pregnant. Sure, you might get lucky, but the consequences of being wrong are huge.

    The LW might want to mention that her friend consider putting the engagement on hold. The stress of doing that is no worse than the stress of her fiancé finding out.

    I’ve been in the friend’s position. Not so much the sex part, but the not telling anyone part. I can assure you it is not a good sign of things to come. I hope she realizes that sooner rather than later.

    1. spaceboy761 says:

      I’m from Long Island. What’s Perkins?

      1. Assuming you’re serious, they’re a chain known for ginormous flags.

        Head to Staten Island. You’ll find three of them there, including one at 1409 Hylan Blvd. 🙂

      2. MellaJade says:

        @ spaceboy761

        Perkins is similar to those ‘Country Kitchen’ type places where you can get the skillet breakfasts…. I’ve lived on both Staten Island and Long Island so I’ve been to both. 😉

      3. Never heard of Perkins. But I so miss Country Kitchen since moving to California! Their skillets are so tasty! In California they try to pretend that everything’s healthy, so the breakfast places here make really crappy skillets with all sorts of fresh vegetables that get in the way of my 1500 calorie breakfast!!

      4. Haahah I was going to say, Joe you might be dating yourself with a Perkins reference – I don’t think there are too many around these days! (at least in any of the places I’ve lived)

      5. I’m not entirely sure I’ve even been to one, but they are still a bit of a cultural reference for enormous flags, I think, and apparently they still have hundreds of locations. 🙂

        And yes, I am dating myself. Honestly, it has solved so many compatibility issues.

      6. Rahmtown_Dan says:

        Perkins: where hang-overs go to die (because you probably just spotted your churchy kin coming in for brunch at the same time you’re heading off to bed)

    2. While I think you are giving the friend WAY more credit than I am… I agree with everything here.

      1. I don’t actually give the friend that much credit at all… but even if she’s just having pre-wedding jitters (which I find highly unlikely), I still think all the LW can do is point out consequences in a gentle way. Anything else will just blow up on her, and, honestly, I don’t think anything she says or does will stop the friend from screwing around. She’s 20, she’s apparently only or mainly just dated this one guy, and she’s looking to see what others are like. She’ll do it now and/or after she gets married regardless, I think, because she is simply not ready to be in a committed relationship, or at least certainly not to him.

    3. Skyblossom says:

      The friend may actually want to get caught cheating so that her fiance breaks up with her. Some women don’t know how to break up with a nice guy.

      1. Skyblossom says:

        I should add I don’t really think he is a nice guy but his fiance thinks he is.

      2. Hey, there are a number of explanations for why a really nice, good guy could start dating a teenager when he’s in his mid 40s. Granted, a small number. A really small number. And there’s a much larger number of reasons why a guy with significant issues would do so.

        So he could be a nice, good, innocent, well-meaning person who genuinely feels he met his match in someone much younger. I just don’t quite buy it, not because I think an age gap always matters, but he was likely one and a half times her age when they started dating and she wasn’t even legal when they met and when he, likely, first started feeling sexually attracted to her. I’m not a lot younger than he is, and high school girls just aren’t appealing. They’re older-versions-of-my-daughters, not hot-women-I-want-to-bed. The thought of actually pursuing one – and I’m about the age he probably was when he started dating her – just makes me shudder.

      3. Oh – before another commenter feels slighted: I’m not railing against older/younger relationships. I just think this one – where even given the benefit of the doubt he was 44 and she was 18 when they started dating – is shady, especially because he was her teacher in high school and is much older. It’s not his age, her age, the age difference, or how they met; it’s all of those things put together.

      4. AnitaBath says:

        Even as someone dating an older guy, I tend to agree with you, or at least see the glaring red flags. At the same time, I can’t help but be reminded of my completely-crush-worthy high school teacher who would be about this guy’s age now.

        She better not be marrying him! >:(

      5. ArtsyGirly says:

        One glaring problem is the teacher thing for me. In school teachers are authority figures – one reason why psychologists say teachers who rape students are particularly damaging to the victim.

        On the other hand I went to high school with a boy whose father turned 90 years old. He had been the mother college professor and they had gotten married before she graduated from college. From all appearances they had a happy marriage from what I saw. I know the dad’s age was hard on my friend because there was always questions about if that was his grandfather and he always had to explain the situation to people.

      6. IMHO, the difference, while small, is that in your friend’s case, his mother was already a legal adult and in college when she met her professor. I realize it’s only a 1-4 year age difference between college and high school, but those 1-4 years mean a whole lot, both legally, and emotional-maturity speaking.

    4. plasticepoxy says:

      love the perkins reference, i knew exactly what you meant!

  6. ReginaRey says:

    LW, I think if you’re looking for something to say to your friend, it should be something along the lines of: “If you are denying to others that you are with him, are thinking of cheating on him, and are unsure of whether you want to marry him or not, then you should absolutely consider ending this relationship.” I actually said this just yesterday…If you are unsure about whether or not to marry someone, it is a SURE sign that you shouldn’t. Maybe your friend needs to hear that from her best friend.

    And as for the cheating, there isn’t much you can or should do to stop it. As sketchy as this may sound, cheating may just be the wake up call she needs to realize that she doesn’t want to marry this man. Support her as you can, but don’t direct her life or her decisions…she’ll simply resent you, and push you away. Best of luck.

  7. If this relationship started after the friend was 18 and no longer in high school, there’s no danger of the teacher losing his job. If it started while she was in high school (it sounds like this is very likely the case), the guy is possibly a statutory rapist or the next thing to it and there are bigger issues. Personally, I would not be maid-of-honor at this wedding. Sometimes being a good friend–including, as Wendy puts it, supporting our friends–means tough love. IMO, being a witness at a wedding constitutes approval.

    1. I disagree with your final sentence, Wendy. I think being a witness at a wedding constitutes support, not necessarily approval. Obviously, if you feel something criminal has occurred, there are other obligations you might have (like, say, reporting it), but not attending a wedding isn’t the way to address them.

    2. AnitaBath says:

      I don’t know, it’s kind of an iffy subject. A similar thing happened at my school (the girl was legal and it was after she graduated), and they ended up getting married. The principal didn’t like it, obviously, and wanted to get him fired, but he didn’t exert the effort. Basically, just because there’s nothing illegal about it doesn’t mean he still can’t get fired. If enough people raise hell and try hard enough, he can be.

      1. Yeah I had a bit of a fling with my high school track coach (after I turned 18) who was also a teacher (but never my teacher) and even though nothing illegal occured, we didn’t exactly broadcast whatever was going on because it didn’t look good and could have had a variety of negative consequences for him…

      2. AnitaBath says:

        Look, you got voted down for being scandalous, maynard! 😉

        Woah, I just got deja vu. I feel like we’ve had this conversation before at TF, complete with people thumbing you down for admitting to having a fling with the track coach…

      3. Probably! That’s cool though. At least I had the sense to go through with my plans for leaving my home town and going to college instead of moving in with him like he wanted! 😉

      4. One thing to remember: the thumbs are close together and especially so when the site is viewed on a mobile device, so it is very easy to accidentally thumb the wrong one.

    3. Not showing up to a wedding as a sign of disapproval creates an enormous amount of bad blood. My father did not go to his nephew’s wedding because he disapproved of the marriage; that was a decade ago and the rift is still healing. There is life after a wedding to be considered.

  8. Of course he treats her better than anyone she has ever been with, she’s 20! That’s like saying your preschool pretend boyfriend is the man of your dreams.

  9. Of course he treats her better than anyone she has ever been with, she’s 20! How many people can she have dated?!
    That’s like saying your preschool pretend boyfriend is the man of your dreams…

  10. Skyblossom says:

    When you friend is saying that she would like to take a break from her fiance I think she is telling you that she would like to break up with him and you should tell her that it is okay to take a break as long as the fiance knows it. Try to encourage her to do this with honesty so that it isn’t cheating and gives her time to think and mature.

    You can’t make her decisions for her or tell her what to do but you can be her confidant and you can give her heartfelt advice in a kind and warm fashion. You can tell her that if the relationship is strong enough to last a lifetime it will last until she is ready to get married, whenever that might be, and if it doesn’t last until she is ready then it wouldn’t have lasted anyway and she would end up divorced. Tell her it is okay to take your time and make sure you are ready and that she can wait to be sure she is marrying the right guy. You can also say that he may be wonderful and treat her well but he still might not be the man for her. The chemistry may just not be there. Tell her that if she has the feelings she’s been sharing with you it may be her subconscious letting her know she isn’t ready for marriage now or maybe marriage to this man.

    I had a roommate in college who cheated on her fiance with the bestman a month before the wedding. I think it was a desperate attempt to stop the wedding because she didn’t know how to breakup with a nice guy that she had pursued and caught. They were divorced within five years and really should never have gotten married.

    As for the 46-year-old fiance he doesn’t sound very mature. Why would someone who is 46 want to spend their time with someone that much younger. The answer is sex. If he matches her on an emotional level then emotionally he is like a 20-year-old and will probably always be on the emotional level of a 20-year-old. She would very quickly mature beyond him and leave him as too immature. She is acting her age and the problem is he is acting her age also.

    1. callmehobo says:

      I’m just gonna go out and say it- flaming be damned-

      Any man that old who is interested in a girl at that age, cannot be a healthy, mature adult. I especially think the power dynamics of the teacher/student relationship suggest that this may be a manipulative man.

      Other than that, I agree with what Wendy says. Stay in her corner, but for God’s sake, try to convince her that she doesn’t need to even step into the ring!

      1. Skyblossom says:

        I agree! I think that being controling and manipulative are immaturity. It’s like the high school girl who constantly bullies, dominates and controls. You hope she matures and most do but some don’t. This guy just has to be immature to pursue a relationship with someone so much younger. He acts like an immature teenager as in many teenagers are already more mature than this.

      2. Skyblossom says:

        To clarify my own thoughts, I don’t think he is able to be in a relationship with someone who is his equal partner.

      3. ReginaRey says:

        I second this. I think that *maybe* a 26-year-age difference can work out on some pretty statistically rare occasions, but usually only when the people involved are much older…say 30 and 56, or 40 and 66. In those situations, at least you can have some confidence that the younger person has experienced relationships with people their age and have become wise and mature enough to make an educated decision about dating an older person. In this situation, however, it seems very unlikely that the LW’s 20-year-old friend has had enough life experience, has done enough dating, and has matured enough to make a HEALTHY relationship work with an older man…especially someone who used to be her teacher.

      4. Anne (I Go To 11) says:

        I agree. I think it’s really bizarre, and that the teacher/student dynamic of their relationship prior to being romantically involved is just creepy. It’d be one thing if they first met each other at a Starbucks or library or *something* other than school…it’d still seem a little odd to me to have such a large age gap, but I’d say to each his/her own. Once you throw in the teacher/student dynamic, it changes the whole game. The fact that he had that kind of power over her when they met just makes me uncomfortable with the nature of their current relationship in general.

        I knew a girl who wound up getting involved with a former teacher of hers not long after she graduated; it was a big scandal because not only was there about a 30 year age difference, but he was also married at the time, and I think he had kids not much younger than this girl. He divorced his wife and married this girl…not sure if they’re still together, because I haven’t talked to her in ages (plus, her younger brother is an ex of mine I’d rather not speak to), but it still caused a whole host of problems for all involved.

        Also, it creeps me out to think that some teachers view their students as sexually desirable. One of my high school English teachers once told us that some of the comments she’d overhear from male teachers ranking female students’ attractiveness, discussing their bodies, etc., in the teacher’s lounge disgusted her. And unfortunately, one of my social studies teachers acted upon his desires and had sex with 2 of his 16-year-old students (this was just a couple years after I graduated, too.) He was married with 2 or 3 young children, too. Needless to say, he doesn’t teach there anymore (and since he had to register as a sex offender, I’m really hoping he’s not teaching ANYWHERE.)

  11. While I agree with Wendy that LW is not her parent and should be very careful about voicing her own opinions as opposed to just provoking some thought in her friend, I disagree that she should have to be in the wedding whether she likes it or not if something did occur. That’s a personal choice for LW, and while she may want to support her friend, I would understand if she felt uncomfortable being the maid of honor at the wedding. Not saying I personally would be, but I don’t think that’s so unreasonable. There are other ways to support your friend in the face of bad decisions without compromising your own feelings, I think.

    1. @Heather: I don’t think that anyone was saying she should feel forced to attend the wedding, just that attending it would show support for her friend but not necessarily approval of the marriage. If she truly feels uncomfortable, she is under no obligation to attend, MOA or not.

      However, I strongly suspect this wedding isn’t going to happen.

      1. MOH, I mean. Too used to “MOA”. 😉

      2. “Be her Maid of Honor; have your friend’s back. If she goes through with her decision to marry, she’s going to need you in her corner, despite how painful it may be for you.”

        That’s what Wendy said, and I just disagree. I don’t think she should have to be in the wedding. Although you’re right, I don’t know if the wedding is going to happen either. I think it would be showing an immense amount of maturity on the LW’s part if she chose to stay in the wedding (granted some infidelity did occur), but I don’t think it makes her a bad friend by any means if she chose not to.

  12. So while I think Wendy’s advice is really good I just have to question intelligence of the LW’s friend. Not really intelligence, but I guess common sense. You get engaged at 20 to a man literally twice your age who you can’t have been (legally) dating for more than 2 years. I’m not saying 2 years is not enough time to know you’re in love, I just don’t think 2 years as a teenager is enough time to know you’re in love enough to get married. She’s having doubts, won’t admit to the relationship, wants to screw around and she still plans on going through with the marraige? I know she’s young, but those are huge, glaring red lights telling her to stop. As for the fiance, he creeps me out. I’m sorry, he just does. As for the LW I think you should speak up and remind her of the consequences but be ready if she doesn’t want to hear it. And I agree with Heather, she’s under no obligation to attend the wedding. Friends support each other but that doesn’t mean you have to condone her behavior. The LW shouldn’t compromise her values for a friend who she feels is making a mistake. She can support her friend and be there for her without being the MOH in her wedding. Maybe that’s what the friend needs, a wake-up call that what she is doing is wrong, and I’m sorry but cheating on your fiance because you’re not ready (no matter how creepy he is) and still marrying him is wrong. Everybody in this scene needs to practice some honesty, no matter how painful it might be.

    1. callmehobo says:

      What usually happens in the bride-to-be’s situation, is that she comes from an environment where she is not given the adequate moral and emotional support to build appropriate self esteem.

      That’s where the high school teacher swoops in. He sees that deficiency in her life, and tells her she’s special and that he loves her, filling in that void. BOOM. Engaged 20 year old.

      I don’t think it has anything to do with common sense, I just suspect that she has been manipulated into this relationship and doesn’t really realize that there are other options at this point.

      1. Good points but the reason why I have my doubts about the relationship and the fiance being manipulative is that there usually is more symptoms to it. I’m assuming that they’re close as friends and if there were underlying issue of insecurity and manipulation I can’t help but feel the LW would have seen it. If he were being manipulative she probably wouldn’t have a FB and if she did he would be monitoring it, he wouldn’t give her a chance to cheat. I’m not saying that it’s not possible and given the dynamics that I see in the relationship I think it’s likely, I just have my doubts because it doesn’t seem like he’s possessive or controlling. Though I always try to remember that all I’m going on is a few paragraphs.
        Also, I just have to jump and say I don’t think the LW is trying to control the friend or taking a “holier-than-thou” attitude. I feel like when she says she can’t let her do it or she would be giving her permission I don’t think she actually means that she has any control over her friends behavior. I think it’s just a phrase that people use when they don’t want to watch someone make a mistake without letting them know how they feel. I can’t control my friend’s behavior but I also can’t “let” her date another douche, meaning I can’t keep my mouth shut and watch her make another mistake. She’s going to do it if she wants but I’ll have done my part in saying that I think it’s a mistake. Thankfully we have a strong enough friendship she understands it’s not meant to be mean or controlling, it’s just meant to be helpful.

  13. I wonder if her friend’s fiance actually wants to get married, or if he is just saying it to keep her quiet, and happy. I would bet that he is the one telling her not to tell anyone about this relationship, because 1.) he doesn’t want to get caught, and 2.) he is probably sexing up some other high-school hotties!I mean it doesn’t sound like they actually hangout in public either which can’t be fun for the girl, not being able to bring her fiance around her friends.

    1. Don’t take this as me in any way defending him, because I’m not (I know nothing of him aside from what the letter said), but… those are some pretty huge leaps there.

    2. AnitaBath says:

      Yeahhhh. It seems like a lot people are making A LOT of assumptions about the guy, based on the absolute zero information the LW gave. Suddenly he’s emotionally stunted, manipulative, a cheater, and a pedophile?

      1. Agreed. While I definitely think the timing and the dynamic of the relationship is questionable, we can’t really make assumptions about the fiance. The only thing we know for sure is that the friend denies her relationship, and wants to cheat on him. Those two issues should be the focus points of the LW’s concern for her friend.

  14. I haven’t read most of the comments yet, but I have to say that even though I only have a few close girl friends, I’m glad that we at least have relationships while we can tell each other when we’re acting completely fucked up.

  15. I’m glad some other people have mentioned that the friend’s fiancé is not a good man. I think the LW friend is starting to realize that her relationship is wrong. I even think the friend has always, maybe subconsciously, known the relationship is wrong by all the steps she’s taken to hide it. The LW should definitely talk to her friend, not about the cheating, because that is a non-issue. The true issue is the fact the friend is starting to realize her relationship is wrong. Her friend needs her more now than ever. That teacher took advantage of a young woman. In studying the ages I think it is likely he dated her before she graduated. They have been engaged for a year and a half. Assuming they didn’t get engaged right away then they dated for two years at least. When she was 18 he was 44, ick! I’m not judging all relationship with large age differences. The issue is the fact she was 18. There is a big difference between 18 and say 25 even. I’m thinking cheating might actually wake the friend up and let her really admit to herself what is going on.

    1. Rahmtown_Dan says:

      …the hell?!
      Where in the letter does it state the man mentioned is “…not a good man”?

      The rest of the advice… i’ll let the thumbs up/down feature speak for themselves.

    2. AnitaBath says:

      Pretty judgmental and presumptuous to automatically assume he’s “not a good man” and the relationship is “wrong.”

    3. Yeah, Monica your letter seems to have a ton of presumptions in it. It is very possible that they began a relationship before she graduated, which would obviously be wrong, but we don’t know that. How can you say that cheating is a non-issue? Regardless of what you think about the LW’s friend’s fiancée, cheating is always an issue. I am surprised that you’re suggesting, if I understand you correctly, that cheating is a proper path to take in this situation because it will “wake the friend up”.

    4. I am sorry I upset people with my opinion. For me there is something wrong with a 44 year old man dating an 18 year old girl. And he is a high school teacher. I was not condoning cheating. As I stated, I think the friend knows her relationship is wrong and will not admit it fully to herself. In this situation only I think cheating would result in the friend realizing what she already knows. The teacher isn’t 25 or 30 but 46! I am 44 and the thought of dating an 18 year old is unfathomable. I would be interested to know if the friends parents know of this relationship. Everything in the letter indicates that maybe only the LW knows of the relationship.

      1. You yourself said the cheating itself is a non-issue, and I disagree. Also, why does it matter if the parents know of the relationship? She’s an adult. If she was 17, then it matters. But she’s not. And we have no proof that anything illegal went on.

        I guess I just think you’re lambasting the LW’s friend’s fiancee, and treating the friend as if she is some innocent little girl who was taken advantage of by the big bad manipulative grown man. Could that be the case? Absolutely. But you are making so many presumptions that quite frankly seem a bit unfair.

      2. I wish you could see past the suggestion of cheating and try and understand what I am really saying. So let me take back my dismissal of the cheating. She shouldn’t cheat she should leave this guy in the dust and go on and discover who she really is as a person. Why the big difference between 17 and 18. So if the teacher started dating her when she was 17 you would consider it suspect but because she was 18 it is okay? Or are you just focused on the fact that she is now 20? I can’t focus only on her current age. I have to take into consideration that she was at most 18 when this relationship started. I ask you what is adult about how this friend has conducted her relationship. Hiding? Lying? The friend is not a mature adult and someone should be looking out for her. I also don’t think the lying and hiding was the friends doing but the teachers doing. Nothing in that letter leads me to believe the teacher has the best of intentions.

      3. Monica, I agree that there’s a lot to be suspicious about, given the fact that she’s been engaged for a year and a half at age 20, so she was engaged at 18 (possibly 19, depending on if she’s just 20 or almost 21) – it sounds like she was engaged to her former teacher almost immediately after graduating. So, yes, it seems odd.

        But… nothing in the letter indicates, to me, that the fiancé is in any way controlling her. He’s not around when she says she’s single. He’s not around when she sees or communicates with ex’s. He’s not going to be around if she starts cheating on him.

        While I agree it’s odd that he’s engaged to her, I really don’t get the feeling that he’s the one in control.

      4. For me she is hiding the relationship because her fiancé is her former high school teacher. That means he is the key reason she is hiding and lying. The hiding of their relationship can’t be unknown to him. I see this girl as the injured party not the fiancé. An 18 year old girl involved with her 44 year old high school teacher is not in control. This girl needs help not judgment. I wonder what she is doing? Going to college? Living at home? Working? She just sounds lost and her friend needs to talk to her.

  16. All I have to say is whoa… Super creepy

  17. AnitaBath says:

    Why is everyone acting like the LW’s friend is the victim in all of this and the teacher is the big bad wolf? HELLO. We know absolutely ZERO about the man, and about the relationship in general. The ONLY thing we know is that the LW’s friend is actively trying to cheat on him. Call me crazy, but doesn’t that make the *guy* the victim? She’s not innocent. How’s about we treat them both as adults, rather than assume the friend is some delicate little flower who’s incapable of making decisions. She’s 20. She’s a grown-ass woman. If she makes bad decisions, she makes bad decisions, but I hardly see how her significant other can shoulder all the blame for them?

    1. ArtsyGirly says:

      Here Here!! I dont like the relationship but that is secondary. The friend is a plane of orphans and puppies about to crash into a mountain.

  18. caitie_didn't says:

    While I applaud Wendy putting the LW in her place and telling her to knock of the controlling tone, I don’t know if I would follow her advice in this scenario. For me, cheating is excusable rarely to never. That’s partly because I’m in the same age group as the LW and her friend- and at this age, we don’t have kids or mortgages or long marriages holding us back from a clean break with someone. So there’s no excuse to cheat, ever. So for me, since I consider cheating to be reprehensible behaviour, I would tell my friend that I would no longer be able to serve as the MOH at her wedding and in fact was re-evaluating my friendship with her. I just wouldn’t want to be friends with someone who treats another human being (even a slightly creepy high school teacher) with such disrespect. Part of being a good friend to someone is being able to tell them when they are being a bad person and I think if the LW is *really* good friends with this girl, she needs to do that.

    But this is my personal belief and the LW needs to decide what to do based on hers.

    1. ReginaRey says:

      I’m not sure that the LW’s friend is necessarily a “bad person” — maybe a very immature, really lost, and extremely confused 20-year-old — but not exactly a bad person. We really know nothing about her, other than what’s written second-hand in this letter. It wouldn’t be wrong for the LW to tell her friend that she is _acting_ less-than-maturely, what with her strong inclinations to cheat on her (yes, definitely creepy) fiance, but to tell her that she IS a bad person isn’t right. When I was 20, I’m pretty sure any one of my friends could have judged me VERY harshly based on my sheer idiocy in relationships, and my inexperience…but thankfully, they supported me, I grew up and out of that mindset, and I still cherish those friends. It might have been different if they went on the attack.

  19. This whole thing is just wrong. From hooking up with a high school teacher, to denying the relationship, to wanting to sleep around – come on now, this is marriage not the Jersey shore. MOH, if you can’t tell your best friend that cheating on her fiance is wrong without her blowing up on you, you should MOA on her. 5 years is a long time to be friends with someone, but if you have to mind your Ps and Qs to the point where you haven’t felt comfortable enough to bring up ANY of your worries and fears for her, then maybe this friend isn’t ready for something as adult as marriage. If she can’t communicate with her best friend, how is she going to be able to communicate with her husband?

    1. Oddly enough, I was telling my boss at work about this letter (I oftentimes read Dear Wendy letters to him to weigh in his opinion) and that’s what he said. He thinks that if LW can’t tell her friend that she thinks that’s wrong and doesn’t support it, then she’s not really that good of a friend if she can’t handle the opinion of someone so close that she chose to make her MOH.

  20. SpyGlassez says:

    Ok, coming from the point of view of a teacher (adjunct at community college) dating a former student younger than myself (though by only two years)……

    This has problems written all over it. Whether she pursued him in school or whether he pursued her, something seems off either way. The age difference doesn’t have to be a negative – my roommate’s parents are about 22 or so years apart in age, my good friend from college married her 20-year-older boyfriend the summer before we graduated – there are other issues at play in this dynamic that distinctly worry me. He was a teacher at her school, she’s denying the relationship and wanting to cheat a year BEFORE the intended wedding….this isn’t healthy for anyone involved.

    However, I also think there’s nothing wrong with the LW stepping down as maid of honor, because the maid of honor should NOT be someone who feels that they are in judgment of the bride. She can indeed support her friend, but she can also tell her that she can’t support her choices.

  21. demoiselle says:

    It sounds to me like the LW’s friend DOES want to get out, but doesn’t know how.

    Is there a reason that the friend feels she HAS to marry this older man? Is he holding something over her head? Does he have some kind of power over her? Scenarios I’m thinking of would include her being kicked out of her house and having nowhere else to go, her having gotten an abortion and he’s threatening to tell her anti-choice family if she leaves him, has been sharing prescription medicine with her, or alcohol, and she thinks she could get into legal trouble, etc . . .

    It might be worth delicately probing whether the friend has any fear of consequences for herself if she breaks the relationship off…

  22. He was her former teacher. When did they start dating? If she hadn’t graduated yet, and they “consumated” their relationship, then legally, that is statutory rape. Her saying that she doesn’t want her engagement to get around because he could lose his job is telling. It tells me that he was seeing her before she graduated. It tells me that he should probably lose his teaching license and is probably still preying on other teenage girls right now.
    Her desire to play the field, as it were, is born out of the fact that deep down, she knows that the age difference is a biggie and that their relationship is wrong. Not because of the age difference, but because of the way it happened.

    Friend – there isn’t much you can do. If you know that she was dating the teacher prior to graduation, you should tell someone. Anonymously if needed. There’s not much you can do for your friend but be a support for her when all of this comes crashing down. If this relationship started while she was still in school, then she is a victim of her “fiance”. She may not see it that way, but she would be.

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