#219: Do I have to tell my boyfriend about an old affair?
Good morning and welcome back to Dear Baby! Today we have a woman wondering whether she has to tell her serious boyfriend about an old affair, someone worried their relationship is falling apart right before they move in together (including their sex life), and a pregnant woman who’s filled with dread and worried her partner isn’t more excited about the baby (including a bonus pic of me pregnant and miserable). Kind of a birds and bees extended cut.
By the way, last week’s find-a-friend comment section absolutely delivered!!! I got multiple texts from friends telling me how heartwarming it was to scroll through and see so many people reaching out for connection. My brother kept telling me he was crying (lol). Thanks so much for participating, I wish you all the best in meeting up! And in case you missed it, we had a great discussion last week on the decision to post (or not post) your kid online. So many high quality comments, so much to think about.
1. On an old affair
“Baby. I can’t give the details you want. I’m sorry!!! I had an affair for about three years before meeting my current boyfriend, about three months of overlap, ended things, and have been with my boyfriend for like three years. A couple of my friends know of this affair but are sworn to secrecy (lol). I have a feeling I will likely be getting engaged soon and want that very deeply!! But ……….does my boyfriend have to know about this deeply flawed part of my past? I’ve never told him and now it just feels irrelevant? But also like this huge thing? Help 🥲”
The tone of this question made me laugh, I will forgive the lack of details. I have to say I was pulled to answer this because I recently went through the process of telling a loved one something that I didn’t technically have to tell them, but which I decided in time felt right to disclose. It did not involve an affair—you win on the drama front. But there are other similarities, so you may find that some of my reasoning applies. Grain of salt though, I tend to lean confessional, so your own nature may lead you to a different conclusion.
This conundrum is interesting because it sits at the nexus of a few competing interests: the right to privacy, the goals of intimacy, the need to move forward. As you consider what to do, I’d suggest avoiding technicalities. For example, you may think your boyfriend isn’t “technically” entitled to your sexual past, therefore you don’t owe him the information. You could also reason the affair “technically” involved your boyfriend because there was overlap, therefore he’s entitled to know about it. It’s not that these aren’t potentially valid arguments—I can’t really say—I just think they feel a little dead-eyed, like you're assessing your intimate relationship through a lawyerly lens. If someone close to me didn’t tell me something because technically they didn’t have to, I’d hope they had other, better reasons for withholding the information. So I suggest you find those, too.
For my own situation, I didn’t disclose the information initially for two reasons: 1. I thought the information could lead to some anxiety for them and 2. I didn’t think they would begrudge me for withholding it. But when more than just a couple friends found out, I was less sure about the second reason. I became aware of the possibility that this person might feel like a fool—in a hypothetical, retroactive sense—to be unaware of something that others knew. This put my protective instinct (reason #1) in a less respectful light. Since some of your friends know about the affair, I think the same risk applies. Consider the reverse: If your husband had a long affair that overlapped with you and some of his friends knew about it while you didn’t, how might this imbalance of information make you feel? Would it depend on how many people knew, or who? There’s a point at which being protective of someone can infringe on their agency—you’ll want to be cautious of that transition.
Then there’s the question of how much you and your boyfriend want to know about each other. As a confessional person, I want to avoid suggesting that maximum disclosure is the surest path to healthy intimacy. Everyone has different preferences. But I do think calling a three-year affair irrelevant or a “flaw” feels potentially dismissive of its importance, and could be a subconscious form of avoidance. If you were to reframe it in a way that truly grappled with the emotional resonance and wreckage of this affair that eventually led you to where you are today, boyfriend included, would that change your assessment? Was the affair formative in any particular way? Might it be worth exploring some of this with your boyfriend, however messy, for the sake of showing him something tender and difficult about your past?
You may feel like I’m overstating the significance of the affair—maybe my impression is actually part of the reason you don’t want to tell your boyfriend: because it will seem like a bigger deal than it was. If that’s true, although to be honest I’d find that pretty surprising, then I think you can stick to considering what maximizes your self-respect, your respect for your boyfriend, and your respect for your relationship with him. I don’t think it’s necessary for our partners to know about every mistake or lesson we’ve ever made or learned, but I do think a healthy intimacy requires, at the very least, a willingness to see and be seen, complications included. Baring your soul can take many forms—in my opinion, the aim is more important than the approach.
2. On painful sex and scary doubts
“Hi Baby, I've been dating my boyfriend for four years. We met in college and we're both 25 now. Our first year of dating was medium distance (one hour driving) and the following year was very long distance. During that time we developed really strong communication and the ability to chit chat for hours. I have always taken so much delight in being with him, even when it was from a distance, and I have confidence in our ability to communicate about almost anything. For the past two years, we've lived in the same city (though not together) and it has been a fun though challenging new phase of figuring out how we can merge our lives and support each other in person. I really do believe that we can live a very happy life for a long time based on what we have built.
However, for the last four-ish months I've been having pain with sex. He has been nothing but kind about it, but almost every time we try to have sex I freak out and cry, basically no matter what we try. We've had candid conversations about what makes me feel so stressed out and what's preventing me from just having a good time. I need to go to the doctor, but for some reason I've put it off a ton, though I do finally have an appointment booked. We've reached a point where he’s insecure that I'm not into him anymore. There have always been people I’m more attracted to, though I do genuinely think no one would make me feel as loved and known as him. However, the thought of being more attracted to other people has been periodically on my mind throughout our relationship. I think this is the one thing I could never address with him.
The final aspect is that in this hard time for our sex life, I've been feeling a strong urge to flirt with other people and developing stupid crushes easily. Sometimes verging into crushes on friends and imagining different lives I could be living by dating different people. I'm trying not to be too hard on myself for this, and I've been trying to keep this under wraps from him (successfully, I think). I know that crushes and flirting happen and can be fun! But I'm concerned that this question of being more attracted to other people will be a continuous problem in the future. Basically...are we doomed?
I'm sure we can find some resolution to this sex issue, but we're moving in together in August and it feels like a very inopportune moment to be having so many doubts and questions. Feeling freaked and antsy about the whole situation, including my own anxiety about it..... HELP!”