29[M] here. Really giving a try with this dating thing. I’ve gone out twice with this woman that I want to keep seeing. We seem to be on the same page about a lot of things. Limited romantic experience for both of us, but want to date. Sexually we’ve had fun once, and want to keep doing that but also the whole learning about each other thing. Aligned goals, home ownership, kids a few years down the line. Aligned values as well which is a pretty big deal to me. She’s told her family about me, and when she told me that I did the same. That doesn’t feel like something you’d do for someone you just like having sex with. Feels a little early, but ive literally never had a third date in my life so what do i know. And here comes the red flags.
This isnt a brag, I’ve had many partners. All of them have been professionals, except one now I suppose. Escorts, service providers, sex workers, pick your descriptor. I feel like I’d be being dishonest if I didn’t tell her that part of my past. Hell it’s only been a few weeks since my last trip into the city to see a provider. And ive got a time scheduled to see one that I now want to cancel. I’m in therapy and my therapist knows about that part of my life, and that I want to put it behind me forever. I can’t see her (therapist) for another 2 weeks.
But it’s also an ENORMOUS red flag I think. Do I bring it up? I don’t want to scare her off. I’ve sunk many thousands of dollars into being more than a little pathetic, in fact it’s the sole reason I’m so broke to this day, but I am on the road to financial well-being. Cash advance on a massive credit limit, horny and lonely is a horrid combination.
I’m seeing her tonight, so I don’t have super long to overthink the hell out of this. I could maybe ask about her immediate deal breakers? And if its one of them, or adjacent to one of them, fess up and get it out of the way so as to not lie and hurt her down the line when it inevitably comes out.
32 comments
I actually am unsure how specific you need to be. I think you need to tell her you don’t have relationship experience but you’ve had many meaningless one-night stands. I would hold the escort information closer to the vest.
Normally I’m all for openness but I don’t think a current partner has the right to pry into the _individual identities_ of your previous partners so long as they are no longer in your life and you’re not in contact with them (this information might also be helpful to include).
I wouldn’t tell her about the escorts and things. Just that you haven’t been in a relationship, which she probably knows already. Just make sure you’re STD free.
But as a woman, if I knew that a man I was dating has done a lot of stuff with different sex workers, I would be kind of weirded out. Not on purpose, but it would turn me off I think. So I’d prefer to not know. Plus, the past is the past. You don’t have to tell anyone about your past. If it comes up, I’d just say you had one night stands that didn’t mean anything.
Don’t lie about anything. Unless you count lying by omission.
It is not being *honest* to unburden yourself of a secret. What you are doing there is hoping to alleviate your own guilt and receive forgiveness from someone who is not yourself. It is not about honesty.
You could tell her the only sex you’ve had has been with pros. You are under no obligation to reveal your sex life before her in any way however, and I’d suggest you don’t. In not revealing anything just don’t lie. Say you’d rather not discuss such a personal detail that involves other people. Or whatever. And similarly don’t want to know her sexual history either
The only thing that bothers me about your story is the implication your sexual history is a result of some sort of addiction. If so, well *that* is a problem. To be clear, having any type of unresolved addiction and keeping it a secret is a huge problem to manage…. not the fact it’s about sex.
Have you been tested for STDs?
If not, probably should do that
“Not to brag” that’s funny
If it does come up, maybe it’s be best to be honest. You seem like you’re in a different headspace now but the last thing you’d want to do is lie when you both touch the subject of the past, if you do. I wish you both well OP
Tell her.
Think about what will happen if somewhere down the line she hears about this from someone else. She will definitely lose trust in you.
Would YOU want to know that piece of information? I don’t think that’s the type of thing you tell anyone, it’s so personal. If the guilt is eating you away, though, I think it’s better to take it off your chest, otherwise it’ll hurt the relationship. But if it’s something you’re only considering cuz it’s the “right thing to do”, just don’t. It doesn’t help anybody, as long as you have done your STD tests and know you’re clean.
I’d tell her before things get too serious, but the way this is ramping up it might be the time now.
Don’t frame it as you’re a terrible person for it, because even you admit it’s a problem and you’re seeking help. That makes all the difference. She might understand and want to be there for you
Idk I would say if you told her, the chances are this relationship would be over. But at the same time, if you keep this from her and she finds out later down the road you’ve wasted her time and yours.
I think it would be good to ask what her dealbreakers are and if sex workers comes up, then it’s better to be honest. Or even what her opinion of sex work is, gage the situation a bit more before you make a decision.
But I would say your past would be a red flag and a deal breaker for most women.
Do you have any friends that know you’ve bought services? If so it might be most prudent to operate under the assumption that she’ll eventually find out and figure out if/how you want to communicate accordingly.
I’m in the “don’t lie, but don’t offer the information” camp. If this becomes a serious relationship down the road, it might be worth examining talking about it, if only because for better or worse, this kind of thing randomly discovered by her ten years from now as your wife could be one of those “I’m out” moments.
I’d want to know and I wouldn’t like it tbh
I will start by saying that its amazing you have found someone you trust, who you want to be open and honest with. That is AMAZING. Keeping doing that!!!
It sounds like you want to tell her about your sexual history… From reading your post, that is what it sounds like. Therefore… You should tell her, because you want to.
Before you do, I might encourage you to question WHY you want to tell her. Are you feeling ashamed of your past? Is it because this is some big secret you are keeping? Are you afraid she will judge you? Is your sexual history something that you think about often?
It seems like this is a need which you desperately want to be met. Nothing wrong with that. We all have needs, and you aren’t wrong for wanting to admit these things and be validated or understood and accepted.
But consider these questions, and mentally, draft your responses to them. Because odds are, she will wonder the same things (although she might not ask them). You, therefore, should jump the gun and show her you have considered how this may look from her perspective, how this information might make her feel… There is a chance she will feel upset, or annoyed, or concerned, or self conscious of her own sexual abilities because of this… And you want to give her certainty that you are responsible and a safe person for her to be with and that you don’t want that life anymore and only want to be with her…
Kind, respectful, nice people respond positively to vulnerability. If you approach her and say “hey, I want to talk about something serious for a moment” she will no doubt get serious and be listening and concerned. That’s when you can tell her “I really like you a lot, more than I’ve ever liked anyone and therefore I am telling you this, WITH THE SOLE PURPOSE of growing closer and hoping we can be 100% honest with each other. In my past (meaning even just a few weeks ago, if that is true) I always used sexual workers and sexual services to meet my sexual needs. I am ashamed of this, and I sort of kept it from you, because of that shame and embarrassment and I was afraid you would hate me for this past behaviour…” You can also talk about how financially it has been a strain for you and admit if you are ashamed of that.
If she is worth her salt (and you phrase it like this, by being honest and vulnerable) she might be upset and annoyed that you kept it from her, and she might be concerned about the money aspect of it, but she won’t leave you… She will tell you that you don’t need to be ashamed for wanting sex, that it is okay. And she will try to do her best to understand, listen and be empathetic.
For reference *(and I fucking hate that I know this information, like wtf mom)* but my own parents dealt with something similar. My dad was spending hundreds of dollars to talk to “sex workers” over the phone (lmao back in the 80s) and my mom was pissed because he kept it from her and because he was so irresponsible with his money. She didn’t really care if he wanted to use porn or whatever, but she was like WTF DON’T SPEND ALL THIS MONEY??? But they worked through that and it was all fine and okay.
I would definitely tell her, maybe it’s early but you might as well.
My ex didn’t tell me until a year plus into the relationship and it really fucked me up.
Good luck op. Hopefully it’s not a big deal.
When you say “aligned values” with this lady. What values are you thinking of?
It’s a good thing you’re self-aware
OP, what does “aligned values” mean? When you say your date’s values align with yours, which?
Some people will see sex work as a professional service, and some will see it as a value of your morality. It will be a real sticking point.
Also I’m concerned that you might have portrayed yourself as “limited experience” already, when you have a lot of experience with transactional sex. You could position these experiences as ONS, but it sounds like you’re seeing some of these providers regularly, so it would be more accurate to say FWB but still not genuine.
To be frank, you may have to quit seeing SWers and get some distance from these experiences in order to date – especially if your proclaimed values don’t align with your actions.
There’s also the risk that you are actually infected but it’s dormant or not yet presenting, like with herpes HSV, HPV and HIV. I would want to know my date hasn’t visited a sex worker for at least a year before I would consider it.
Honestly, you don’t need to be dating right now. The reason why people are saying this sounds like an addiction is because you literally dug yourself into deep debt to continue satisfying your need for sex. That looks a lot like an addictive behavior pattern.
Continue seeing your therapist and ask them if they think you are ready to date yet.
Personally, I would want to know that information before I even sleep with someone. However, it’s not on my list of deal breakers and I haven’t even thought of asking a partner that until years into the relationship at which point the answer didn’t even matter.
I think it’s too early maybe to show that vulnerability of yours, for me as female 30 y/o a red flag would be that the guy brings this conversation on the third date. I would really question what does it mean and where I am getting into…
I would chill, and little by little get to know her better and open yourself up as well.
All of us have things that could be red flags so, chill
Damn. That’s a tricky one…
It’s not about dating a guy who’s been sleeping with escorts, it’s about dating a 30 year old man, who:
1. Wasn’t able to form a relationship ever before.
2. Wasn’t able to form strictly sexual relationship with anybody.
3. Wasn’t able to settle down to jerking off, even when his finances were at risk.
4. Is poorly managing his money.
5. Is risking STDs and risking I get it, too (did you know that cervical cancer spreads even if a man uses condom?).
6. Doesn’t care about who he’s sleeping with (aside from looks, maybe).
7. Doesn’t care if woman he’s sleeping with is truly enjoying the experience (you can never be sure with escorts).
8. Doesn’t need established trust between him and his sexual partners.
Like cmon, it’s different if you’ve done it once or twice, out of curiosity, or in some desperate times, but to go this far you need to have moral code very different from mine, which isn’t necessarily bad, but would be a deal-breaker for me. You’ve in debt because of it, which means you’re addicted. Not to sex, but to escorts, to the lifestyle. I wouldn’t trust you wouldn’t come back to it if we had a crisis in our relationship, or if you were depressed, for example. I wouldn’t want to risk it. And she may not want to risk it, either. It’s like hiding active heroin addiction. It is morally wrong to hide it, but I understand why one would such thing. I’d probably hide it, too, if I were you.
If I were on your girls’ place and you wouldn’t tell me, I’d be absolutely livid you omitted this information and would seriously weight the relationship, ultimately deciding if lying on top of being an addict are enough to break up with you.
If I were on your girls’ place and you would have told me right away, I’d be livid and probably brake things off immediately.
I honestly think you have a lot of time to discuss it with her, I’d wait at least for 6 months of serious dating until bringing it up, so you can honestly say you weren’t ready before, but you know it’s not fair to keep it hidden. Even then, I’d portion the topic into few separate discussions. It may still not be enough, and if that’s too much too handle for her – you’ve got to respect it.
It is indeed an enormous red flag, you even said it yourself. Why would you want to hide it from her? That is really not nice. She deserve to be able to know all the truth, who you really are, before she can decide if she wants to be in a relationship with someone like you.
What I see as a red flag is you are still seeing these sex workers while saying you desire a serious relationship with this girl, not so much that you have been with a sex worker.
I feel like the bigger issue is that you went into debt to continue seeing these sex workers. Thousands of dollars? That sounds like an addiction, and you should probably work that out in therapy before dating anyone.
If you’re not comfortable disclosing something about yourself, then you’re not ready for a partner. You shouldn’t be withholding in order to get someone to like you or stay with you. You’ve done what you’ve done, you are who you are and the right partner will accept you.
That being said, it does sound like an addiction and something you should work through with your therapist before you bring someone into the mix. It has nothing to do with the sex work, and more to do with how you went into debt for it and how it’s negatively affected your life. You may think, “I have a partner so I’ll be better,” but you have to first work through your shit to be better for yourself.
Honestly, as a woman, if the person I was seeing didn’t tell me that they saw tons of sex workers and planned to, I would end the relationship. The lying is a bigger red flag to me than seeing escorts. Obviously I wouldn’t be like “yay, the person I’m seeing sleeps with random sex workers!” but it’s better than lying.
The sooner the better, imo.
I (29/f) would rather be told my partners history from the getgo rather than once I’m already invested in him. Not saying that she’ll be scared off but the least you could do is be upfront about it.
I met my bf (34/m) a year ago on tinder and while he never saw any sw, his sexual history is definitely more adventurous than mine. He told me about his escapades on like… our second or third date. Did it bother me? A bit. Was it a deal breaker? No. It’s impractical to be dating in your late 20s and expect to find partners with no past history of their own.
I dunno man, you should be honest. Most people ask someone there dating about their sexual past, how many partners you have slept with etc. it definitely tellings of someone’s character. I think that person your dating has a right to know. But it sounds like you have an addiction. If a guy told me her slept with…let’s say 150 girls, I would be turned off…vs a guy told me 30 girls.
If you want to date this girl seriously you need to stop and cancel any bookings you have. Why are you paying sex workers? Why not just do Tinder hook ups?
Honestly you should just be honest with her and tell her. One thing I loved before getting with my boyfriend was his honesty. He was never ashamed of what he did and always took responsibility.. it’s her choice to make if she wants to continue being with you after she finds out and I also think she deserves to know your past..even if it doesn’t define you it for sure has a big influence on what type of person you are today. If she sees the change and chooses to love you anyway then you’d also be at ease and not have to worry that maybe one day she’ll find out and feel like she’s been with a total stranger up until then.
I think there are a few problems here. The first problem is that you’ve only gone out with this woman twice. Unless you’ve both been struck by Cupid’s bow of love, you’re nowhere near the point where you need to discuss your history (at least this kind of history). It’s up to the both of you to decide if and when to disclose certain things.
The other issue is what others have been saying here. If you’re dating someone, don’t even consider seeing a sex worker. Sex workers’ services should only be used when someone is completely single. That’s the red line (forget red flags).
For those of you judging OP for utilizing sex workers’ services on a regular basis: I call bullshit. You don’t know OP. You don’t know what he’s had to deal with in his life. OP specifically mentioned he’s in therapy. There’s nothing to be ashamed about when it comes to addiction. It’s a disease just like any other. What started this process? What caused OP to continue with the process? NONE OF YOU KNOW.
As for the self-identified sex workers dismissing OP as a potential life partner, I say: SHAME on you. This is your profession that you use to make a living. If there’s no shame in you doing the work, then there’s no shame in someone enlisting your services. You may or may not have sex with a dozen men a day. How is it worse for someone to enlist the services of a sex worker every couple weeks? You can’t have it both ways. The BIG difference is a lot of lonely men go to sex workers for companionship and intimacy that they have otherwise been unable to find elsewhere. Sex workers are mainly doing their job to make MONEY. While I respect that, I find it absolutely intolerable for anyone working in the sex industry to look down upon someone like OP because of the frequency and duration of his utilization of sex workers’ services.
The biggest advice I can give OP is get tested for all kinds of STI’s before having sex with this woman again. If you come out clean, move forward and never mention your past. ONLY tell her if it comes up in your conversations. It’s not like you’re asking her about any and all sexual interactions she’s ever had.
Rant over.
You need to be sure you have no STDs. However, I do not advise talking about any past sexual partners nor should you ask about her past relationships. What is past is past. Either of you talking about past lovers will tend to bring issues up that will end the relationship. Work through your own issues with your therapist but don’t bring your partner into therapy with you. It doesn’t matter why you had sex in the past. It matters that you are monogamous now with this girl.