“I Regret Not Having an Affair When I Had the Chance”


Art by Andrew Condell

My colleague, “Maria,” and I are both married to different people. There was a spark between us and I found her very attractive. She made a move on me by inviting me to her place while her husband and kids were away. Even though I am very attracted to her, I did not take her up on it. Since then, she has made several advances which I have not pursued as I worried about the potential consequences of an affair. Her advancements went on and off over a 15-month period until she eventually stopped.

All the time, deep down, I wanted to be with her and my mind was going crazy thinking about her, but somehow I resisted the temptation. She and I mostly work from home, but every so often we’re both in the office together, and I feel the spark again and my feelings reignite. Now I look back with regret that I did not take her up on offers. I finally spoke to her and told her I had feelings for her. She backed off, telling me she is happy where her life is right now. She also sounded angry when she rejected me.

I kind of knew in my heart that she would turn me down as time had passed by. Now I feel embarrassed as I feel our friendship is over. Even though I look back at the opportunities I passed up, at the time I was happy with my decision. Why, all this time later, do I regret it? — Missed an Opportunity for an Affair

I’m not going to give you a hard time for having feelings for someone other than your wife. The feelings sound superficial enough – you mention nothing about Maria at all except that you find her attractive — and you didn’t act on your feelings despite what you perceived as countless invitations over the period of many, many months. So, I guess, kudos for that?

What I will give you slack over is regretting not having an affair and for sharing your feelings with Maria. I mean, no shit, Maria sounded angry that you finally confessed your feelings. For one thing, you may have been wrong about what you thought were advancements on her part. I admit, it sounds a little shady that she invited you to her place when her husband and kids were out of town, but perhaps you misperceived the invitation? Maybe it was merely a friendly invitation? Maybe she wanted to discuss work in a more comfortable environment than the office, especially considering neither of you works in the office regularly and both of you consider your respective homes places of work. Imagine how she might feel if, for well over a year, you misconstrued friendly professionalism as flirting and sexual advances and then told her as much! Pretty angry.

But maybe you’re right and Maria was hitting on you over and over and over for many, many months despite your both being married and despite your being colleagues and despite your constantly rejecting her. Finally, she decides she’s done trying and she puts thoughts of an affair with you out of her mind. It’s THEN — when she decides to give up after a very long, concerted effort to seduce you — that you finally admit that, well actually, you liked her all along?! How do you think she’d feel? Probably pretty angry — and not just at you. She’s probably pissed at herself and for good reason — all that time spent pursuing a married man and threatening her own marriage as well as her career. What a stupid thing to do.

And, now, finally: your own regret. Regret for what? For not breaking the vows you made to your wife? For not risking your job, your family, your whole life, really, for some sex? Come on, you know you made the right decision. And you only finally confessed your feelings to Maria when you knew it was unlikely she’d be responsive since so much time had passed. I suspect you only admitted your feelings to her when you did to extend the spark of excitement — to tug on the status quo of your day-to-day life that, if you’re like most people, can feel mundane and monotonous.

You didn’t really want an affair – not a physical affair anyway – but just the continued idea that you could have one because that’s exciting and fun. Instead, you were shut down — the invitation to pursue something elicit yanked back, kicking you out of a multi-month daydream that you were special to someone other than your wife — a daydream where the dull demands of day-to-day married life cease to exist and the thrill of something forbidden fueled you through each boring day. That’s your regret. And, oh yeah — a ruined “friendship” with Maria.

Focus on what you get to keep instead for rejecting an opportunity to pursue an affair: your wife, your family, your job, and, hopefully, some self-respect. I promise, losing any of those would not have been worth the momentary — the very temporary — thrill of an affair. If you crave excitement — if you need to shake up your life a bit and remind yourself you’re still alive, and if you need to threaten what you hold safe and dear in order to do that: go sky diving. At least then you have a parachute to break your fall.

***************
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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.

38 Comments

  1. LW1: if you speak of your respective spouses as “other people”, well, you have work to do. My guess is that you are bored to death to work at home and you focus on a fantasy and lame flirting. Your mistake was to confess your “feelings” – how much do you know her anyway? It happens to fall on a crush like this but this is all about your own personal crisis. Change something in your life, your focus, and focus more attention on “people” who really love you.
    LW2: why are you so much in this baby-sitter presence? She is there to substitute to the parents presence. Stop taking her as your personal support system. YOu are both so inappropriate. Especially as you just have your third child: your poor wife. Be professional with her: don’t answer personal messages, only professional ones, and remain cordial.

    1. As to your comments about why he is in this babysitter’s presence so often, there are many circumstances when this would happen. As I just wrote below, we have an au pair for our twins. Yes, she lives here, but even if she was just a regular sitter, I’d be around all the time when she was watching the kids since I work from home. There are all sorts of circumstances where a child care provider could be around while one of the parents is also around.

      1. Avatar photo Skyblossom says:

        My cousins worked from home and hired a sitter to watch the kids while she worked. I think it’s becoming a common situation.

        They also may be in a situation where dad gets home before mom and the oldest child has an activity that he will need to drive her to so he is there with the baby sitter for a while and then takes the older child to the activity without having to drag around the younger two kids.

      2. Ok, may be. But this guy needs to avoid her company. We didn’t see those messages she sent him, but the friend’s wife did, and she saw the excitment on the receiving end. Her reaction says something. He should take care and check his loyalties. I don’t know something lower than flirting with the babysitter.

    2. As a 33-year-old woman who has spent half of her life babysitting and working with children, there are certain families you develop a very special bond with. You grow to love their kids as if they were your own, especially if you’ve known those children almost all of their lives.

      Some of these family members are incredibly grateful and appreciative of how much you also love their children. It isn’t out of the ordinary to develop bonds with them also and become close. This usually happens with the mothers for me but it doesn’t seem out of the ordinary that it might happen with a father. Some people are very warm and kind and it seems that’s what this young lady is. I don’t think it is necessary to keep a cordial/ formal relationship when a family sees the babysitter as part of their family also. That is what this situation feels like to me.

  2. I have an au pair right now who is also 23 and gorgeous. She sends me texts with hearts in them all the time. Wow, I never realized that she is flirting with me! I mean, I do look pretty hot walking around the house in my ratty bathrobe and unbrushed hair. Here I was thinking she was just being nice….

    Wendy is right, that is how young people text these days. I guarantee you my au pair has no interest her 46 year old host mom. As for your wife’s friend, some people look for mal-intent everywhere. If there are no other signs that this girl is flirting, and the only indication is a few hearts in some text messages, I can also guarantee she is not.

    1. dinoceros says:

      Obviously we don’t know her sexual orientation, but if she’s straight, then her texting you that way is different than texting a dad. I assume you interact with women you know in a different way than you would with men, but maybe I’m wrong.

  3. I don’t agree that LW1 was misinterpreting his colleague’s advances. That seems really odd to say. His colleague was angry not because he misinterpreted, but because he turned her down so often. She’s an asshole. LW1, here’s a hint: not a good idea to have sex with people who have no moral compass whatsoever. You want to blow up your entire life? Why?

    LW2 seems to be going on and on and ON about this babysitter. Dude, she wasn’t flirting with you, but you need to take a LARGE step back anyway. It shouldn’t even be crossing your mind to compare yourself with her boyfriend, jesus. Help. Your. Wife.

    1. Bittergaymark says:

      LW1). Yeah. I didn’t get where that came from either… she was pissed about being rejected. That much was VERY clear.

  4. Both of these letters made me feel skeevy all over. LW1, it’s all about you you you in this letter. GROSS. And LW2, you want your friend’s wife to be right a little too much. Also GROSS.

    Both of you: You need to take all this fantasy energy and instead invest it in appreciating and spicing up your relationship with your WIFE. Or you know, you could just burn your whole life to the ground bc your ego needed to be stroked. Your choice.

  5. I think that it’s possible that the babysitter is a bit infatuated with him or I guess personally attached to him. That doesn’t mean that she is flirting.

    I also don’t see the point in crapping on the husband as being unappreciative of his wife. The wife isn’t complaining about his interactions with the babysitter. There is no indication at all that the wife is not supported either logistically or emotionally. The wife’s friend made a specific accusation and he wrote in about it. He’s clearly flattered by the idea of a younger woman liking him but there are no signs in the letter that there’s anything wrong with his marriage or the way he treats his wife.

    1. Bittergaymark says:

      Yeah. Lots of projection going on in this thread…

  6. LW1 – doubt she was flirting. Guys always think someone is flirting when they are just being nice.

    LW2- baby sitter wasnt flirting, just doing the typical emoticons they do and being nice. Dad is gross for even comparing her boyfriend to him, which makes me think he is considering making a pass.

    Both men are terrible , feel sorry for their wives.

  7. I think both of these LWs just had a taste of what it used to feel like to be desired. I am older and a mom and i am not getting hit on any more. When it happens, it catches you off guard and is flattering. But don’t give up everything to regain that feeling.

  8. LW2 – You obviously have a crush on the babysitter. You state you have your “humor going for you” going for you (why?), you talk endlessly about her, and are comparing yourself to her boyfriend (why does his job pay better than yours when he’s only 23?). You obviously want your wife’s friend to be correct. You don’t even ask if she’s flirting so that you can fire her it’s all for your ego.

    Focus on your wife, the one who is no longer 23 and has bore three of your children. Making googly eyes at the babysitter is beyond inappropriate.

    Keep all your responses professional and try to leave this young girl out of your fantasies.

  9. Sea Witch says:

    I wonder how LW1 would feel if his wife decided to take an “opportunity” to have an affair with another man? Shocked to the core, no doubt.

  10. dinoceros says:

    LW1: I don’t think this is regret. I think it’s wanting what you can’t have. Suddenly, Maria became irresistible when she was no longer throwing herself at you. Also, whatever discomfort or unhappiness you have in your life causing or stemming from your marriage issues are making you look for something to be sad/mad/whatever about. If it wasn’t this, it’d be something else.

    LW2: Doesn’t matter if she was flirting or not. I think that’s what guys don’t get and which ends in them all claiming that other girl is FOR SURE not flirting! Your babysitter, particularly one that you spend several sentences talking about how pretty and awesome she is and how much she likes you, should not be texting you lots of compliments and emojis. I’m not sure if you truly don’t know that or if you’re just playing oblivious. It’s not appropriate. Your commentary on your babysitter should be related to whether she’s good with kids and does her job right. Once you start spending more time watching her for her looks and stuff, then you’ve turned it into something weird. Tell her you’d like to remain professional and won’t be texting outside of work-related issues. If she doesn’t comply, then you need a new babysitter.

  11. All good points, but I want to answer some of the comments as well.

    Thank you for answering my email. I appreciate all the comments as well. I wanted to answer some of them.
    LW2: why are you so much in this baby-sitter presence? She is there to substitute to the parent’s presence. Stop taking her as your personal support system. You are both so inappropriate. Especially as you just have your third child: your poor wife. Be professional with her: don’t answer personal messages, only professional ones, and remain cordial.
    • Excellent question! At first, we hired her because my oldest had joined soccer and my wife works Saturdays. We’d often be late because getting my oldest and her little sister dressed, ready to go, and there wasn’t really fair so after a while I gave in and agreed that we could interview some people to help out. The only time I have spent the entire time with her and the kids was the first time she started. I watched how she interacted with them and I was around to answer any questions she had. Once my wife became pregnant I took on an extra day of work as “work from home” because her maternity is unpaid time and we’d need the extra money. The normal routine right now is that I take my girls to soccer since they both play Saturday mornings. We get home, they change, I feed them lunch, the babysitter comes so that is when I begin working from home. Anytime I get a break, I give “Gloria” a break as the kids are usually knocking on the door/window asking me to come play, push them on the swings, etc. My youngest is very attached and is a daddy’s girl so she especially will ask the babysitter constantly when daddy can come outside. I spend the fifteen minutes with the kids and the babysitter, and I will chat. Then I go back inside and normally won’t see her again until I tell her she’s free to go.
    When Mom is working, she gets home around thirty minutes after the babysitter leaves. When she started maternity leave, she used the extra time to get some rest. Now that the little one is here, she wanted to keep the babysitter as we had a large construction done on the house and she likes having the time to get the house back together without having to keep stopping because the kids are running around.
    On days when I am finished early, I let “Gloria” go home early. I don’t have her spend any more time at the house than she is needed.
    The girl my wife originally wanted to hire, before “Gloria” interviewed, was the same age and she was very attractive. I spent a day with her and the kids as I did later on with “Gloria” and she was on her phone too much and I didn’t feel the girls should have to try three to four times to get the babysitters attention if they needed her for anything.
    “Gloria” also doesn’t watch the baby. Where is the baby while she’s here? With me in the home office. It is easier to keep giving a child a pacifier or a bottle than keeping kids that can walk/run around from touching buttons. My wife takes him for a few minutes while I go play with the kids for a few minutes.

    As for your wife’s friend, some people look for mal-intent everywhere. If there are no other signs that this girl is flirting, and the only indication is a few hearts in some text messages, I can also guarantee she is not.
    • You just described my friend’s wife perfectly and that is exactly what I said about the hearts.
    LW2 seems to be going on and on and ON about this babysitter. Dude, she wasn’t flirting with you, but you need to take a LARGE step back anyway. It shouldn’t even be crossing your mind to compare yourself with her boyfriend, jesus. Help. Your. Wife.
    • I did go on and on about the babysitter…. because that’s who the question pertained to and I gave details to help my question be answered as accurately as possible. If the question was about someone else, they’d also be the main character, no? As I stated, I too did not/ do not see this as flirting so I agree with you. As far as helping my wife, since I am assuming you feel she was barefoot, pregnant, and mopping the floor or cleaning dishes, here is my daily weekday routine. A few things different now with the baby, but the rest is the same:

    o My wife does overnight feedings since I have work in the AM.
    o I get up at 5:15AM and either run or do weight training for a little while.
    o I get my son from our room and take him downstairs, so he doesn’t wake my wife when he wakes up. I change his diaper and prepare a bottle. (Normally he stays asleep in this bouncy chair he has).
    o Afterwards I make sure that the oldest one’s lunch is made, backpack has everything in it she needs, all papers I need to sign are done, etc.
    o Next, I make sure my youngest daughter’s bag is ready for day care.
    o I shower and get dressed for work.
    o The girls are up at this point, so I make sure they are dressed and give them breakfast wile I feed my son.
    o Next, they brush their teeth.
    o I wake my wife so she can watch the baby while I take my oldest to the bus stop. My wife is up, takes our son, and goes back to bed.
    o Once the bus picks my oldest up I go back to the house, get my youngest, and drop her at day care.
    o I leave day care and go to work.
    o After work I pick my daughter up from day care and then stop and get my oldest from aftercare.
    o When my wife is working this is when I’d either pick up dinner or make something. My wife would be home about twenty minutes after the rest of us. When she is home this is where I go home and play with my son a little while as my wife gets dinner ready.
    o My oldest does her homework, I play with my younger daughter and baby, and then they change, brush teeth, go to bed (this can take a while though).
    • My wife does a lot on Sundays so I am not saying I do 100% of the work because that would be absolutely false. It’s a tradeoff and I just happen to be the one that has a little more time than she does when she is working.
    LW2, you want your friend’s wife to be right a little too much.
    • Sure, it’d be a confidence boost, but not something I would risk losing my kids, wife, house, money, and life for. I have two friends going through divorces right now for that very reason (one of them it was their fault, the other the wife cheated) so I see up close what happens when you play with fire. I have also been cheated on in past relationships and I know the hurt it causes.
    I think that it’s possible that the babysitter is a bit infatuated with him or I guess personally attached to him. That doesn’t mean that she is flirting.
    • Possible I guess, but I don’t think I am around her enough for her to form any type of attachment. I don’t even know how she’s seen enough the last eight months to say I am a good father.
    I also don’t see the point in crapping on the husband as being unappreciative of his wife.
    • I can understand it. The cliché labels the father as doing nothing and the mother as doing everything. Funny too because I am the one that changes 90% of the diapers, I do the wash, dishes, etc. I let the girl’s help, too so that they know there is no such thing as a ”man” job or a “woman” job.
    LW2- baby sitter wasnt flirting, just doing the typical emoticons they do and being nice. Dad is gross for even comparing her boyfriend to him, which makes me think he is considering making a pass. Both men are terrible , feel sorry for their wives.
    • I often feel awful for her. Especially when I volunteer to watch all three kids for three days in December so she can go to a Christmas party with college friends in another state because after carrying our son for nine months I figured she could use a mini vacation. Days I have had the kids (1, 2, or now 3) by myself in the last six years? 12. Days she has had the kids all day without me being around at all? 1.
    • Remember, my wife knows what I was asking. She read the question above that Wendy answered. She’s read the comments. None of this is behind her back.
    • Comparing is gross? If you see two cars and you have a choice between a new car or one that’s rusted out with broken windows and flat tires you wouldn’t compare them before making a choice? It’s human nature to compare things and people.

    I think both of these LWs just had a taste of what it used to feel like to be desired. I am older and a mom and i am not getting hit on any more. When it happens, it catches you off guard and is flattering. But don’t give up everything to regain that feeling.
    • Never give up a good thing for a good time.
    • It would be off guard because again there would be zero inclining to me that it was possible, it’d be completely unexpected, and it would be flattering. I wouldn’t expect a 23 year old to be interested in the slightest at an older man with three small kids and
    LW2 – You obviously have a crush on the babysitter. You state you have your “humor going for you” going for you (why?), you talk endlessly about her, and are comparing yourself to her boyfriend (why does his job pay better than yours when he’s only 23?). You obviously want your wife’s friend to be correct. You don’t even ask if she’s flirting so that you can fire her it’s all for your ego. Focus on your wife, the one who is no longer 23 and has bore three of your children. Making googly eyes at the babysitter is beyond inappropriate. Keep all your responses professional and try to leave this young girl out of your fantasies.

    • A crush? Maybe love? Who knows. I fall easy. I am crushing on you right now.
    • Wouldn’t “ego” be more like “of course she likes me. Why wouldn’t she”?
    • “You don’t even ask if she’s flirting so that you can fire her it’s all for your ego.” – not 100% sure what you’re saying here, but if I was to ask her and she isn’t (which again I am sure she’s not) that constitutes sexual harassment these days and I am also not looking to make her feel awkward or uncomfortable.
    • Money and looks matter. Admit it or not it does. You don’t trade gold for silver.
    • His job pays better because his father owns a well-known NY based company and he, at 23, has a job high in the company and he has stock options. Chances are if you have ever sent flowers you have used them at least once.
    • I am not sure you read it correctly as you say my wife’s friend when the question clearly states “my friend’s wife”.
    • The talking “endlessly about her” is again because that’s the basis of the question. Want me to talk about one of the pets and then randomly ask the same question about the babysitter?
    • Didn’t know you could see my goggly eyes through the computer screen….that is beyond a skill!

    LW2: Doesn’t matter if she was flirting or not. I think that’s what guys don’t get and which ends in them all claiming that other girl is FOR SURE not flirting! Your babysitter, particularly one that you spend several sentences talking about how pretty and awesome she is and how much she likes you, should not be texting you lots of compliments and emojis. I’m not sure if you truly don’t know that or if you’re just playing oblivious. It’s not appropriate. Your commentary on your babysitter should be related to whether she’s good with kids and does her job right. Once you start spending more time watching her for her looks and stuff, then you’ve turned it into something weird. Tell her you’d like to remain professional and won’t be texting outside of work-related issues. If she doesn’t comply, then you need a new babysitter.
    *She is pretty and she is an awesome person. I dont know how I kept saying how much she likes me when I have said in my question that I don’t think she is flirting.
    *The emoji’s isn’t being oblivious. It’s like wendy said in the answer. I figured that’s how people her age text now.

    1. Oh my God, keep a professional distance from the girl and maybe consider seeing a counselor about feelings of resentment towards your wife (a rusty, busted car? Seriously?)

      Combined with your gushing about the nanny being a perfect, natural, Madonna-esque vision with your baby, you seem to hold some bitterness about having to share housework and childcare, and altering your work arrangements – newsflash, that’s called being a parent. You don’t get to entertain questionable fantasies about potential employees because your wife expects you to pull your weight and not leave her to be the sole caregiver.

      Keep that professional distance, and if she crosses a line, have your wife talk to her about professionalism (it seems like this is not a task you have the subtlety to sensitively handle). And for crying out loud, give your wife her three days off without being such a martyr about it!

      1. *He*is the rusted out beater. Four different people jumped on him for comparing himself to the boyfriend. That’s what he was responding to.

      2. Fair dues. The substance remains.

      1. To clarify: What the fuck was that mess of hot vomit I just skimmed?

      2. Netter4733 says:

        Called answers baby…..mwah

      3. “A crush? Maybe love? Who knows. I fall easy. I am crushing on you right now.” That’s not creepy at all.

      4. golfer.gal says:

        Sooo your wife is the rusted out beater car in this situation?

      5. *He*is the rusted out beater. Four different people jumped on him for comparing himself to the boyfriend. That’s what he was responding to.

      6. If “Netter4733” is the LW, which obviously, wow, this makes you sound even weirder. “Baby? Mwah?” No one needed your “answers.” No one wanted 100 paragraphs of deranged musings on the hotness of the babysitter and her boyfriend, and how you feel terrible for your wife but also parenthetically you do more work than her.

        Marriage counseling.

    2. That’s… a LOT more words than someone who actually didn’t care would use to talk about a situation in which they claim they didn’t care.

      I feel sorry for the poor woman, sitting here while her every minor move is being dissected and discussed by some creep she’s trying to be friendly with because she’s watching his children.

      1. Yeah, methinks he doth protest too much. Even if that is the way “the kids” text these days, he needs to draw a line between himself and his employee. As someone who has worked on many sexual harrassment lawsuits, this situation is ripe for misunderstanding. Always err on the side of caution.

      2. Hey, this guy’s wife, if you’re reading this, get hubs some help, he sounds absolutely deranged in his update (hint, that’s because Wendy has a length limit for submissions but here he was free to go on as long as he wanted about how awesome and pretty “Gloria” is and how hot and rich her boyfriend is, and how he feels sorry for you). This is an embarrassment.

    3. This is a lot of words, but literally everyone jumped to a bunch of weird and unwarranted conclusions from the first letter about how he was ignoring and failing to support his wife so it’s not surprising that he’s a little defensive about it.

      1. I didn’t. I didn’t even comment on his first letter. I was like, whatever. But he sounds psycho in his update. Who talks like that?? Thank god none of the men I know.

    4. Yup you definitely have a crush on this girl, and your looking for validation that she has one back even though you wouldn’t act on it. I get it, it makes you feel good. I’m guessing validations a big thing with you since you sound like your looking for it here for being a dad and are probably looking for it from your wife at home for being a dad as well, but you don’t get it because well it’s your job to be a dad. Then comes your attractive babysitter and she gives it to you, and now you got all the feelings for her, and if you know that she feels the same way even though she has a dime piece at home that would really make your day!

      No she doesn’t have a crush, she’s good at keeping her job. She can see how you react to her compliments so she keeps then coming.

    5. LW2: so what was your question again? You seem to have all of the answers in your reply! I’m guessing, however, you didn’t like the fact that most replies were not very generous towards you.

  12. LW1: Let’s assume for a moment that you’re right and Maria, a married woman, really was putting the moves on you, a married man. Is that a person you’d want to be with?

    LW2: The babysitter isn’t flirting. At worst, she is being unprofessional. Someone should tell her that she shouldn’t send her employer heart-emoji-filled texts. Your are not her friend, you are her boss. She’s young, though. You’re supposed to know better. And frankly, you do sound like you wish a 23-year-old woman was into you.

    It sounds like both of these LWs have some issues in their marriages that need to be addressed.

  13. anonymousse says:

    LW 2-The thing is, if you didn’t care you never would have written in. If you didn’t care and didn’t want to entertain the idea of blowing up your marriage and life, you would ignore the emojis, keep it strictly professional and/or even find a new sitter.

    I truly doubt she is flirting, at all.

  14. LadyPants says:

    Ha. LW1: My best friend and I had a way of describing your type of guy. It’s called “She Talked To Me!” This is somehow interpreted to mean we’re now in a “dating relationship”. I’ve had to file two restraining orders over this nonsense. The message to other ladies being- stay the fuck away from insecure men! She probably didn’t ever want you, and if she did you turned her down. LWS , she’s angry, You fucked up on way or another. Give her feelings respect. If you can manage it, save a little for your life partner.

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