How Do I Handle Retroactive Jealousy Over My Girlfriend’s Sexual History?

How Do I Handle Retroactive Jealousy Over My Girlfriend's Sexual History?


Estimated reading time: 14 minutes

Dear Dr. NerdLove:

I am a 68 year old man, dating a 59 year old woman. After dating my girlfriend for almost a year and a half she told me that she had 5 or 6 threesomes in her past. This occurred when her husband was ill and gave her permission to seek satisfaction outside of the marriage. She got on Plenty of Fish and hooked up with a FWB that after a while proceeded to set up MMF threesomes. They both enjoyed the one-on-one sex and the threesomes for about 6 months or almost a year. His illness got worse and she walked away from that lifestyle.

She says it was just sex with FWBs, very detached. They hardly ever kissed, rarely spent time outside the hotel room etc.

Her husband eventually passed and she didn’t see anyone for 8 years before dating me. I really value this relationship and need to process this information that she’s shared with me.

I seem to be experiencing retroactive jealousy over something I had absolutely no control or involvement in. Need help dealing with my jealousy so I can continue to grow this relationship.

The Past Is A Foreign Country

What you’re experiencing is called “retroactive jealousy”, TPFC. Usually when we experience jealousy in a relationship – something that happens to everybody – it’s because of something happening either in the present or in our shared past with our partners.

Retroactive jealousy, on the other hand, involves feeling jealousy over experiences that your partner had long before you two ever met, never mind started dating. And while it’s tempting to write retroactive jealousy off as insecurity and tell people “look, build yourself a bridge and get over it”, it’s worth digging into.

More often than not, feelings of jealousy are the “check engine” light of relationships; they’re a signal that something is off, somewhere. But, like the check engine light, that doesn’t mean that the “something” is serious or threatening. Just like the check engine light could mean that your engine is about to drop out of the car if you drive over 55 MPH or you didn’t tighten the gas cap until it clicked, sometimes those feelings of jealousy may mean that there’s actual danger to the relationship… or it may mean that you’re feeling an unmet need somewhere.

This is especially true when it comes to retroactive jealousy; after all, it seems a bit silly to feel upset about things that were done long before you two were an item. How rational is it to be upset about somebody’s actions before you two were in a relationship? But as the saying goes: your feelings are valid.

That is: the way that you feel is valid. You are definitely feeling the thing you’re feeling and people can’t tell you not to feel them. That doesn’t mean that the reason for those feelings are sensible, logical or even real.

So, much like when dealing with contemporary jealousy, it’s worth digging down and figuring out just why you’re feeling the way you feel. What, precisely, about your girlfriend’s sexual past is bothering you so much and why?

Folks who, for example, feel threatened by a partner’s past relationships are often dealing with issues in their own lives, often in their own pasts. If they had a partner who cheated on them with or left them for an ex, then seeing pictures of their current partner with someone from their past might bring up the worry that they might get hurt again.

Getting hung up on a partner’s sexual history is another common source of retroactive jealousy and also tends to involve issues from that person’s own past. Sometimes being aware of their partner’s sexual adventures in previous relationships can affect the idealized image of who their partner is. Other times, it could mean that they feel inadequate; their partner had all these crazy adventures with people before now, so why not with them? Or it could bring up feelings of not being able to measure up, not being able to perform to the same standard or simply feeling as though being more sexually experienced gives them an edge in the relationship… somehow.

Does that make sense? Of course not. But that’s jealousy and insecurity for you; if it made sense, I’d be out of a job.

So, right now, you’re feeling jealous and weird because your partner – with her husband’s permission – had some wild times, including threesomes with two men before she started dating you. The place to start digging would be exactly where those negative feelings start in that sentence. Which part of this is the trigger? The fact that she was married at the time? The fact that her husband was chronically ill at the time? Could it be that he gave her permission to go seek sex outside their marriage because he was ill? Was it the fact that she had an open relationship? Or is it the exact acts that bother you? Would you feel as jealous if she had been with a hetero couple instead?

To be clear: I’m asking you these without judgement. There’s no right or wrong answer here, no choice in this that is more acceptable or less bad. It’s not about “well, if this is what’s bothering you, that just means you’re a bad person”, it’s about figuring out what’s making that check engine light come on so it can be addressed.

It’s also possible that you may not know, precisely, what the issue is. It could be that the whole thing is tangled up in your head and you may knee-jerk to an answer just to have one. Landing on “she had threesomes with two men” would be an easy one to default to, especially if you grew up with the idea that women are less sexual than men and that women aren’t supposed to be sexually adventurous or that sleeping with two men, instead of a man and a woman or two women, is somehow dirtier or more degrading.

But the fact that culturally this is the easier answer doesn’t mean that’s what’s actually bothering you.It could well be, for example, that you worry that this means that if something happened to you – you were stricken with Long COVID or became bedridden or disabled – that she’d leave you to be with someone else. Or you might worry that the fact that they opened their marriage means that she can’t or won’t be satisfied with a monogamous commitment. Or you might feel left out; she had these great adventures in the past, but seemingly has no interest to have them with you.

This is why it’s important to dig deep and not just immediately assume that the first thing that comes to mind is the correct one. There’s a saying that I like: your first reaction is what you were taught; your second reaction is how you actually feel. Separating your actual feelings from what you were told to feel is incredibly important.

Take some time and put some serious introspection into this. Once you feel like you have a pretty good grasp on what’s actually bothering you about this, then it’s time to start processing and handling things.

Now, depending on what, precisely is triggering these feelings for you, there are a few things to do. If, for example, you’re feeling retroactive jealousy because of past traumas in your own relationships, the most obvious answer is to talk to a counselor or therapist to help heal those particular wounds. On the other hand, if the issue is that you feel insecure in your relationship – you worry that this means she will cheat on you or that you won’t be “enough” for her – then you should talk a little with your partner about those feelings. Letting her know that you worry about this and you’d appreciate a little reassurance or for her to love you a bit louder when those worries crop up can help ease the fear that her past is an inevitable future for you.

You should also make a point of doing some things that make you feel good about yourself. Much of insecurity, especially when you find yourself feeling jealous of past exes or past experiences, comes from how you see yourself. Doing the things that make you feel good about who you are, whether it’s dressing better, accomplishing some goal or just finding things that make you feel like a sexy badass, help ease the feeling of not being “good enough”.

 In those cases, yes, some reassurance from your partner can help… but only if you believe her. And it’s a lot harder to believe that she means it when she says you’re enough or all she wants when you don’t feel that way about yourself. So, like the hot dog vendor said to the monk with a fifty dollar bill: true change must come from within.

The other thing I would suggest is to sit down with your partner and talk about those experiences. Not so much in the nitty-gritty ‘Dear Penthouse’ way, but about what those experiences meant to her, how she feels about them now, and so on. You want to be non-judgmental and accepting in these conversations; after all, you want her to be honest with you, not just telling you reassuring things that you want to hear. Knowing how she actually feels – if, for example, she would ever want to have those experiences again, or it was a “glad I did it, but that’s done now” – can help you get more of a handle on your own feelings. Knowing how she feels about it all helps chase away the whispers from your jerk-brain that say “she’s just waiting for a chance to cheat on you” or “she’d never be that adventurous with you.”

The thing to keep in mind, though, is that this is a you problem, not a her problem, and it’s not on her to solve it for you. Her past may be the trigger for these feelings, but they’re your feelings, and that means you have to be the one to resolve them. She can help by giving you the extra love and support you need on occasion if those feelings flare up, but you’re the one who has to manage them, process them and ultimately resolve them.

Now, the good news is that if you treat this as an opportunity for growth, you have the chance to turn this discomfort into a moment to improve and strengthen your relationship. Open, honest and non-judgmental communication are all vital parts of a successful relationship, as are being able to express your needs, worries and fears. But so too are acceptance and understanding – both of your partner and her past, and of yourself. Keep that in mind, and you’ll find that you and your partner will have a relationship that doesn’t just succeed but flourishes.

Good luck.

Dear Dr. NerdLove:

Me and this boy (lets call him Jake) have been mutuals for little more than a year now. We have gotten closer in the past 3 months. We have been in 2 friend groups together and I began developing feelings for him. Our mutual friend had informed me that Jake was going to get with some girl that is best friends with my best friend and that made me jealous. The girl he’s going to get with (lets call her Lea) is honestly such a pretty girl but I know she’s somewhat of a mean person. (my best friend knew I liked my crush and went behind my back and set her friend Lea up with Jake).

I know I’m an asshole since I’ve gotten with other people before, one of them being Jake’s friend and now that I feel jealous because he’s getting with Lea is unfair on my part. Jake has always commented on how he’s attracted to Lea and I don’t know what came over me but I just texted him “don’t get with Lea.” He asked why and at first I decided I wasn’t going to tell him, but then my friend convinced me to and so I did.

I told him I liked him and I got friend zoned which I saw coming. I told him it was not my place to comment on who he gets with and he said it was okay. He asked to be chill but he won’t even look at me or speak. I wasn’t even looking to date Jake or get with him or anything I just wanted to get my feelings out there. But now it’s weird between us. I should’ve known this would happen. Where do I go from now and how do I restore our friendship?

Stuck In The Middle

Man, I do not miss high-school. I never really grok the folks who talk about high-school being the best time of your life; the constant confusion and anxiety, the never-ending arbitrary (and often self-imposed) “rules” that governed every social interaction… it’s all just drama, often for drama’s sake, put on because everybody’s confused, nobody knows who they are and they’re all just bumping into everyone else while trying to make sense of it all.

And honestly, there’re few things worse than having a lot of weird feelings had having absolutely no idea what to do with them or about them and then just flailing around trying to do… something, and only realizing after the fact that you had no goddamn clue what you wanted or expected in the first place.

Ok SITM, here’s what’s up. You like Jake. You felt a little possessive about Jake because you liked him. Your friend setting Lea up with Jake felt a little bit like a betrayal, because you had that sense of “ownership” over him, and his getting with Lea – with your friend’s assistance – violated that feeling of “dibs”.

The problem is: your feelings for another person don’t grant you any inherent rights over them. Liking someone doesn’t give you the right of first refusal in their relationships, nor does it obligate them to like you back or to seek your permission before going with someone else.

Similarly, your friend going “behind your back” feels like a betrayal because how could your friend do you dirty like this? But again, I refer you to what liking someone does and doesn’t do. It can feel somewhat callous – your friend had to know this would hurt you – but they were actually being somewhat more respectful of the fact that Jake’s an autonomous individual, not someone who can be claimed. Jake, it seems, already was interested in Lea. That would indicate that your friend wasn’t “going behind your back” so much as helping facilitate something that Jake already approved of.

It also ignores that your friend didn’t exactly act alone. Jake, too, was directly involved in this. Jake wasn’t helplessly caught up in sneaky, shameless manipulation that he didn’t have the wherewithal to resist; he was an active participant. He could easily have not gone along with it. Instead… well, he apparently liked Lea differently from how he liked you, and the rest is history.

(I’d also be interested to know if your friend acted unprompted, or if Jake asked for their help.)

Once you see all of that, it all becomes much simpler to understand, and it tells you what your next steps are. I suspect that at some level, you spoke up less to get your feelings out there and more to stake your claim of ownership of sorts; even if you didn’t get a boyfriend out of this, at least you would keep him from being with someone else and you’d still “have” him, as it were. Recognizing that and being honest about that are going to be important moving forward.

What you have now is an awkward situation, made more awkward by the feeling like this is more about alliances between quarreling factions in Fire Emblem  than relationships. Jake is undoubtedly feeling weird about the whole situation and doesn’t want it to get any weirder or more uncomfortable.

The first thing I would suggest is that this would be a good time to call out the awkward and confront the feelings of shame you’re feeling head on. I’d recommend laying this out to Jake as an apology; you were feeling weird about him possibly seeing Lea, you got in the middle of it and now it’s awkward and you’re sorry. Let him know you’d still like to be friends, that you’re willing to power through the awkward if he is, and then make like Elsa and let it go.

That is, you do exactly what Jake asked: be chill about it all. Being chill, in this case, means that you let him decide if he wants to continue being friends, and give him the space to do so on his timeline. If that means that he doesn’t want to talk for a bit… well, it kinda sucks, but let him have that. Be polite, be friendly, but if he’s going to be distant, then just allow him to be distant. You already inserted yourself into a choice he was making for himself. Demonstrate that you understand what went wrong by not repeating that mistake.

Don’t mope, subtweet or otherwise get angsty on social media about it – certainly not places where he’s likely to see it or connect it with you. That can feel manipulative, especially when you’re young. Feel the fuck out of your feels, but do it in your own space and on your own time.

Remember: this happened because you got in the middle of something that ultimately wasn’t about you. It was about him and Lea. An apology and explanation – one that makes it clear that you understand that this was a you issue – will let him know that you’d like to still be his friend. That puts the ball in his court. When and if Jake is ready to be friends again, he’ll let you know. But it has to be his decision, and he’s going to have to be the one to make the next move.

Good luck.