“My Boyfriend is Deployed and I Found Craigslist Messages in His Email”

My fiancé of four years is a captain in the Air Force and just deployed. While using his laptop for schoolwork, I ran across emails and multiple nude photos of women. After searching a little deeper, I found that these photos came from Craigslist ads that he had responded to. Not only did he respond, he gave out his number and had them text him these pictures which he then forwarded from his phone to his email. I’ve discovered that he has been doing this for years. He has responded to ads about sexual massages and even tried to set up a meeting (I can’t tell whether the meeting actually happened or not). He was also sent on a TDY to Las Vegas on the military’s dime and used the Craigslist there to meet up with women for “happy endings.” What makes it worse is that he flew me out a few days afterward to spend time with him. I then ran across multiple emails from dating sites he was registered on. I know most of his passwords and was able to log into the accounts and read the messages, and I saw that he even got about forty phone numbers. I actually took it upon myself to deactivate all of his dating accounts and message the women to let them know the truth.

How can someone live under the same roof as you and your son and do these kinds of things behind your back while carrying on like everything is fine? Is this some kind of psychological disorder than can be treated with therapy? This is just a shock to me, but I can’t exactly bring it up while he’s deployed overseas and has other people’s lives in his hands. I could bring it to his dad’s attention in hopes that as a team we can get him some help. And he blames me for us not being married yet! Now I know why we aren’t married and it isn’t my fault at all. — Captain’s Girlfriend

Absolutely do NOT bring this to his dad’s attention!! It’s none of his dad’s business! If you’re worried about upsetting your boyfriend while he’s deployed and “has other people’s lives in his hands,” imagine how much worse it would be having his dad all up in his business, trying to “get him help.” No. Don’t do that.

I can’t tell you whether your boyfriend has a “psychological disorder” or not, but I can tell you that YOU have a problem, and its name is “untrustworthy boyfriend.” Thankfully, there’s a cure! It’s called moving on already. You’ve given this relationship four years and it’s not working. There’s no fix here. Your boyfriend pursuing sex workers and (many) other women is only a symptom of the problem(s). It’s not like if that issue can be addressed — and that’s a big if with no short-term or long-term guarantee — everything will be all honky-dory. You’ll still have whatever problem(s) existed in your relationship in the first place that led to your discovering about his indiscretions by snooping through his email. In addition to your boyfriend needing to stop screwing around behind your back, you’d have to work on your communication issues, your snooping, your lack of trust, and whatever else has been holding you back from progressing to marriage, which you seem to want. It’s been four-plus years and you’re not there yet, and it’s not just because your boyfriend has a thing for happy endings with random women in Las Vegas.

When a relationship doesn’t work, it’s never just one person’s “fault,” and this is no exception. It’s not working because you aren’t right for each other. I know that’s a bitter pill to swallow, especially when you’ve invested so much time, and you have a child, too, whom your boyfriend is at least a father-figure to, if not his actual dad (unclear from your letter). But that’s not a good enough reason to stay in a relationship that isn’t working. And your boyfriend’s being deployed also isn’t a good enough reason to stay in a relationship that isn’t working. Life isn’t put on hold during a deployment. You aren’t under an obligation to the country, or even to your boyfriend, to pretend for another year that you’re still committed to this relationship that has run its course.

Your boyfriend is a captain in the Air Force; he has trained for challenges. He has prepared for the physical and emotional demands of deployment, including the pressures it puts on one’s personal life. If he couldn’t handle an emotional set-back like a break-up, he not only wouldn’t have made it as far as he has in the military, but he also would’ve put a ring on your finger a long time ago in an effort to try to lock things down, so to speak. Don’t use his deployment as an excuse to delay something that will be hard for you. You gotta get through it, feel the pain and disappointment, learn from your broken heart, let it heal, and then move on to something better. There IS something better, I promise. But you’ll never find it if you don’t let yourself.

I’m a 19-year-old girl who finished high school two years ago. I have a full-time job as a legal assistant. Shortly after I started, I was chosen to be the legal assistant for a new attorney in the office. I had no experience whatsoever, but I got the hang of it pretty quickly. The new attorney (male) and I got super close, and in November he asked me if I wanted to stay at the firm with him since he was going to rent it out for a year. I thought about it and decided sure, why not. There are only three other employees. I’m the only girl there, and I do pretty much everything. So far in these past four months, he’s given me a total of, like, $500 in little bonuses. No one else gets bonuses. He also paid for my paralegal course which was $1500. Is that normal? He’s 33 and about to get married because his religion and mom are kinda forcing him to, but I feel like he has a crush on me maybe. Am I being crazy? He might just care about me, right? Since I am so young, he might see me as like a little sister? Or do you think he likes me? — Paralegal in Doubt

I’m not sure I understand the progression of events in this situation — you moved with the new attorney to a different firm? The original firm dissolved and he decided to start his own at the same office? Regardless of the details, you are his subordinate, along with what sounds like two other people, and you are getting special treatment that makes you uncomfortable in that it raises questions about WHY you are getting such treatment. You are wondering if some sort of line is being crossed, and you are well within your right — legally and morally — to find out. So ask him! Say, “Hey, I’ve appreciated the bonuses and payment of my paralegal course, but I’ve noticed that the other employees haven’t gotten the same benefits. I was wondering why I’ve been chosen and not the others?” It also wouldn’t hurt to find out what the expectations are for you in return for his paying for your paralegal course. Are you expected to continue working for him for a certain length of time? And what entitles you to bonuses? Staff-wide clarification on bonuses, payment of courses, payment tiers, and work exception (especially since you say you do everything!!) needs to be communicated, so that everyone is on the same page and no one feels singled out for “special” treatment.

But beyond all that, you need to follow your gut. If you have a feeling this guy likes you, maybe working for him isn’t the right thing for you. Whether the feelings are reciprocal or not, working for someone who’s romantically involved with someone else, in a situation like you’re describing, is asking for drama. And as a naive 19-year-old with very little life or career experience, it doesn’t sound like you’re up for the challenge of drawing boundaries and making clear distinctions between a friendly professional relationship and something more. And make no bones about it — when the lines become blurry, as it sounds like they are, it’s YOU who will be in trouble, both emotionally and financially (in the sense that it’s your job that is most at risk). Basically, to continue on as you have, when you have suspicions this guy has feelings for you, is playing with fire, and I don’t get the sense from your letter that you’re well-prepared to handle that. I’d start looking for a new job ASAP.


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


  1. LW1: Don’t try to “help” him. Leave him now, as Wendy said.

    1. Scarlet A says:

      100%. He doesn’t have a disorder. His disorder is that he’s a shithead. If you confront him he will swear up and down he’ll never do it again and then promptly do it again.

      Source: Divorced from CL cheater hopeful.

  2. Skyblossom says:

    Whose blaming you for not being married yet, the dad or the fiance?

    Leave the dad out of this. You can never solve a couple problem by trying to get the parents involved.

    Since he just deployed you have some time to decide what to do. I suggest you get some counseling to figure out how you reached this point, what things have you not been noticing and what to do now.

    Once you’ve decided what you want to do you can act. You don’t need to wait until he returns. He owed you honesty and fidelity and cheated instead. You don’t owe him a year of your life on hold. I’m guessing he won’t be as upset as you imagine. There is a reason he’s been putting off getting married and it’s probably because he doesn’t want to be married to you but doesn’t know how to break up. Maybe he purposely left something on the laptop so that he could be gone when you found out and you would be gone by the time he got home. I think he saw this deployment as an opportunity to end the relationship.

    1. I thought that too. All that stuff was on the laptop and so not hidden that she could just run across it? And she knows all his passwords? Sounds like he kind of wants to be caught.

      1. Skyblossom says:

        It seems coldly calculated to me.

      2. artsygirl says:

        He also would have known in advance that he would be deployed so it wasn’t like he didn’t have time to either erase all of the evidence or password protect his computer.

    2. You would be surprised how lazy cheaters are about infosec. The governor of Alabama and Gavin Rossdale both had their cheating revealed (separate affairs, not each other) because they had their cheatery cheater text messages syncing across all the devices in their family’s iTunes account. People are dumb about these things.

      1. Avatar photo Cleopatra Jones says:

        But a lot of times, they subconsciously want to be caught so they are lazy.
        We had a family friend that kept trying to tell his spouse that he was unhappy (she got pregnant after they agreed to break up when they were dating). She kept wanting to work on it, and when he would get the courage to leave she use the kids to guilt him into coming back.
        He had affair after affair to force her to leave. He didn’t even try to hide it. The affairs went on for a few years. He finally decided to end his marriage cause he said he needed to get out because he was so unhappy.
        He remarried a few years later, and you can’t even get him to look at another woman. He absolutely adores his second wife, and they genuinely have a good relationship.

  3. artsygirl says:

    LW1 – you fiancee is a dick who cheats on you. Dump him and move on, there is no fixing this. I will disagree with Wendy slightly when I say that this relationship is solely ending because of your fiancee’s actions. Also please get tested!

    LW2 – I am not sure what to make of your letter. Are the other three people in the firm lawyers or on the same level as you? If you are doing all the work then it makes sense you would get bonuses since law firms often award bonuses as part of the pay structure. Furthermore, many businesses pay for further training for their employees if it benefits the office – which seems to be the case with your paralegal course. None of the things you state in your letter suggest that he has made any personal purchases, inappropriate comments, or other overt overtures towards you. I get the feeling that you have developed a crush on him and are hoping that his courtesy towards you actually signals personal feelings. I am not sure what to make of your comment on him being forced to get married.

    1. flowerchild says:

      LW2- There’s 3 of us. I am the receptionist and legal assistant. The other 2 people are the accountant, part time and we have a “runner” he basically just goes and gets whatever we need at the office or if we need any documents from clients, he’ll go get them. He hasn’t made any bug personal purchases but every time he travels, he always bring me a little souvenir, only me. I haven’t developed a crush, but i feel like he has. You just know when someone has a crush on you, like they way they look at you, but i don’t know i just feel like he does. He’s Indian and even though we don’t live in India, his family still follow the religion, so he has to marry an Indian girl who his mom chose out. Crazy, I know, but I respect every religion. He was super indecisive about marrying the girl, like he even showed me a pros and cons list of her, like he kept asking me if he should marry her and I would just tell him to do whatever he felt was right. He also invited me to their wedding which will be in Cancun, Mexico and his mom even made me an outfit, but I don’t know if I will go, because I was the only one invited and he hasn’t told me that I could take my boyfriend and I don’t want to go alone.

      1. artsygirl says:

        Ah so the little gifts is a bit more personal but might be anything from general kindness to him lightly flirting. If it is making you uncomfortable, I would ask him to stop it – otherwise, why borrow trouble? The wedding invite is a bit problematic. How soon is the wedding in Mexico – sounds like it might be fast approaching since the mother has made you an outfit. Have you already said yes? If so, you should go with our without your BF- if not, it would be completely within your rights to ask if you BF is also included on the invite.
        PS Indian (Hindu, Jain, Sikh, and Muslim) weddings are literally the best! I have been to a few and they are wonderful parties filled with delicious food, infectious music, and really fun hosts who will bend over backward to show you a good time.

  4. LW1: I’d say get some counseling. I cannot comprehend why you, instead of just being mad and leaving, are trying to figure out how to get him help. Is this a self esteem issue or what?

    LW2: I think personally you are reading into this. Paying for a course for an employee to do work you want them to do is hardly special. Also you likely have no idea what bonuses others receive. Perhaps if it is only you who get them it is because you do everything as you say. Also don’t look a gift horse in the mouth.

    1. Texican Ashley says:

      Agreed. Your lawyer boss paid for a course to teach you how to do your job at his office? Strange! In regards to the bonus, based on the description they gave above they are the only full time person doing legal work, so it makes sense the bonuses would go to her. Like the lawyer wouldn’t give the accountant a bonus as they are more on the same level professionally and the number of clients doesn’t significantly impact his work. Also, I worked for an Indian doctor and whenever he’d go to India he’d bring back little trinkets for the office staff. He was very kind and did little things for us all the time. It was nice but I never mistook any of his kindness as hitting on me. The fact is, it seems you are good at your job and he wants to keep you around. Don’t mess up a good situation!

  5. Avatar photo Guy Friday says:

    LW2, I can’t say for certain whether or not there are feelings on his end. There’s no real way for us to know. But let me say this: as the managing attorneys of a small firm, I HAVE paid for training for younger attorneys and support staff; as artsygirl pointed out, it benefits me to have them better trained so I don’t have to show them how to, for example, properly draft discovery demands or interrogatories. I have ALSO paid bonuses — be they buying lunch or cash or gift cards — out of my own pocket to said people when I feel like part of my win on a case was because of work they did. If you spend 10 hours digging through crates of paperwork and find me the smoking gun that forces the other side to settle, I don’t care that I could technically say “well, it’s her job”; in my mind, you deserve a cut — even if it’s a little cut — of my profits, because you were an asset to me. And, yeah, sure, some of it is with a certain expectation of loyalty to me and the job, but I think that good bosses reward their employees when good work is done to show them the bosses are grateful for their hard work, and I know when I was an employee I turned down lateral moves to other firms because I liked where I was working. I will also say, however, that I had a situation two years ago where that behavior was misinterpreted as advances, and even though I put that to bed quickly when I found out by saying “I’m sorry if I gave you the wrong impression, but this was simply as an effort to show gratitude for your work” I had an intern quit on me after 3 weeks because of that.

    So, yeah, it can be hard to read, and I know that, but I still do it because I don’t want one person’s misinterpretation to change what I believe is the right thing to do for staff. If you’re actually uncomfortable with receiving bonuses, you can ask him to stop; I find it hard to believe he’s going to refuse to not give people his money. But the fact that he does it does not inherently mean he wants to sleep with you; it’ll be the context of things that will ultimately determine that. Still, keep in mind that every state bar has a lawyer regulation board and ethics rules that prohibit “offensive behavior” (which is a deliberately broad thing), and trying to seduce your staff would likely qualify as such if you filed a grievance, so if he crosses the line with you don’t feel too intimidated to let the state bar know.

    1. flowerchild says:

      LW2- It just seemed a little weird to me that he was only giving me bonuses and not to my other 2 co workers. On this last bonus, he gave me a check and on the memo, it said “1 of 9 bonuses”. When he gave me the check he told me that it was for my hard work because he knows that I’m basically the one that does everything for him and his brother. I think I was just over thinking, because my previous boss who i was with for a year (my first full time job) only gave me a Christmas bonus, so this just seemed odd, but now I feel a little more calm knowing that you also give bonuses when cases settle. Thank you

      1. Avatar photo Guy Friday says:

        You’re welcome 🙂 And as for the souvenir comment you made on artsygirl’s comment, I think it depends on the souvenir too. If it’s something he spent less than $10 on because he thought you’d like it, I wouldn’t think of it as a big deal.

        It’s weird to people, but law is SUCH a stressful job — especially as a solo/small firm practitioner with support staff who rely on your success to get paid — that sometimes lawyers like to just do random acts of kindness to show “Hey, look, we’re not always grumpy and crabby and stressed.” I came back from hearings today to a gourmet cupcake from one of my associates, who got me it for no other reason than she passed by the shop and figured I’d had a rough week and could use a pick-me-up. Her husband, by the way, is amazing, so I have no concerns she wants to jump all over me 🙂


  7. I used to work for a doctors office, and the first doc would buy the staff lunch, gave me a card with money on my birthday, moved to another office and the doc bought me a program to learn Spanish. Doctors and lawyers make a lot f money, and they both rely on their staff a lot to have their day run smoothly. I took those gestures to mean they wante to invest in me and or they appreciated my work. If the lawyer is other wise professional, I’d take it as a compliment. It wouldn’t hurt though if bonuses and training was outlined in a handbook, both forbyourself and coworkers

  8. flowerchild says:

    LW2- It just seemed a little weird to me that he was only giving me bonuses and not to my other 2 co workers. On this last bonus, he gave me a check and on the memo, it said “1 of 9 bonuses”. When he gave me the check he told me that it was for my hard work because he knows that I’m basically the one that does everything for him and his brother. I think I was just over thinking, because my previous boss who i was with for a year (my first full time job) only gave me a Christmas bonus, so this just seemed odd, but now I feel a little more calm knowing that you also give bonuses when cases settle. Thank you

  9. golfer.gal says:

    LW1, you absolutely can bring it up while he’s overseas. The reality is he’s been cheating on you in various ways and with literally dozens of women over the course of many years. Does he have a personality disorder or some other psychological issue? Maybe. Maybe not. What is sure, though, is that lying and cheating that runs this deep has an almost 0% chance of changing. It’s safe to say he won’t stop.

    You need to make an appointment with your doctor asap and get tested for every std. I also second the suggestion of starting therapy. I know it’s hard to imagine leaving, but it’s your only option, and you damn sure shouldn’t wait a year to even bring it up. You need to start the leaving process now. Do not stay with this man. He may cry, or promise, or get angry and try to blame you. Don’t give in. Move on with your life. You and your child deserve better

  10. I just gave my clerk $200 today for a massage since this week sucked and was filled with stupid people who stressed her. I bring her souvenirs from my trips and buy her lunch at least once a week. If we have a busy week I add a couple of hundred extra to her pay. I have other staff that I buy lunches for but they only get a bonus at Christmas and it is way less than hers. But she is also the one that runs the office and gets things done even if it means sneaking in on the weekend. She is the reason I get to work from home at least 2 days a week (and spend that time with my toddler) and I have no intention of losing her. Maybe because we are both straight women it is clear that it is just me showing my appreciation for her. Maybe where there is a chance of impropriety you have to go that extra mile to keep things professional. The only part that was concerning was the piece about his mother and religion forcing him to marry. How do you know that? If he told you then that was a line crossed. And if you surmised that then you are too invested and are assuming things. Take a step back.

    LW1 – what is there to salvage? You don’t have children together so consider this a bullet dodged. There is no illness that makes men cheat. No medical intervention to help you. No intervention at all… so don’t tell his dad. It is a choice. His choice. To get happy endings. To have dating profiles. To sext other women and meet up with them. He cheats. Regularly. Get checked by your doctor. Move on from him. If you want to move on and tell him when he returns home then fine. But move on.

  11. Findingtheearth says:

    LW2: I’ve worked in the legal field for 8 years. Good legal assistants are hard to find and keep as the job is emotionally and mentally demanding.

    I often received bonuses, lunches, dinners, etc. both lawyers I worked for brought back souvenirs when they traveled. Ones wife made it a point to ensure I got something on secretary’s day and the holidays.

    I think it’s normal. Hard work should be rewarded.

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