Are Honesty and Dating Incompatible?


I wrestle with the idea of honesty in dating a lot. Whoever said “honesty is the best policy” didn’t really grasp the subtleties of dating in the modern world. Or courtship in general. Maybe an increased focus on honesty would make us all better daters, or maybe we’d be miserable from all of the constant honest rejections. Maybe it’s easier to deal with a rejection when someone does something hurtful without explaining themselves, like ghosting, and maybe being told “I just don’t find you attractive or engaging” would just be too painful to hear every time you get rejected. I want to talk about honesty in the holding yourself accountable to being honest sense, because that’s something that I still don’t know where I stand. Let me start by saying that personally, I don’t think that honesty is inherently bad or good. I also don’t think that being dishonest, or acting in bad faith is inherently bad or good. Take what I say with a grain of salt, but I tend to look at honesty, dishonesty, and bad faith on a case by case basis. Sometimes a lie is the more moral thing to do, depending on the circumstance.


With that caveat aside, I really want to get to the heart to the matter. Can an honest approach to dating actually work? At what point does playing your cards close to your chest move into you being dishonest? What should you or shouldn’t you disclose when dating?

Let’s start with an easy one: Honesty regarding your sexual history. I tend to lean toward partial honesty, or an honesty regarding the important factors. I think that if you have anything in your sexual history that might put someone else’s health or quality of life at risk, you need to disclose that information prior to sex. That includes any STDs/STIs you might have, and I say that with no judgment for those who may have an STD/STI and I’m aware that there is a large amount of stigma around someone’s status, but I think that if you’re about to have sex with someone, disclosing whether or not you might put their health, or even just their quality of life at risk, then you have to be honest about it. With that said, I’m also of the mind that you don’t need to disclose things about your sexual history that would pose no additional risk factors to a partner. If you’ve slept with 100 people, have been tested and continue to get tested after your last sexual partner and pose no risks to the person you’re going to sleep with, you don’t need to disclose your number. If you’ve slept with 5 people, all of whom you did not use condoms with, and you’ve never been tested once, ever, you need to disclose that information. Being honest about sexual history is easy (as an idea at least, though maybe not in practice) because it’s a matter of asking “Will being dishonest put them at risk?” and choosing what to disclose based on that information.

A little less easy to answer is how to be honest about your dating past. Let’s say that you’ve had a relationship in the past, were hurt in some way, and now you’re dating someone new. How much do you disclose and how soon do you disclose it? How much can you disclose before you’re crossing over from being honest to being the person who rants about their ex? I think that there’s no right answer for everyone, but part of me wants to say that you should be as honest as the situation calls for. If it’s a first date, you probably shouldn’t get into the details of how your last relationship ended so much that it ended and now you’re ready to date. If someone asks on a first date why you’re single and the real answer is “my cheating ex suddenly left and stole all my furniture”, maybe the right thing to say is “I had a tough breakup but I don’t want to dwell on it” and disclose more if you make it past the first date. It’s not wholly honest, because of the omission of some very important information, but I think that what you tell people should be dependent on your relationship to them. A first date with a stranger is not the time to say “full disclosure: All of my exes were horrible people and one of them tried to stab me”. While it might be true, telling a stranger intimate details about you is usually going to come off as off-putting. I’m using dating past as an example, but if you told someone about any source of pain in your life and how horrible it is on a first date it would raise some read flags. Again, the rules about danger/risks applies if your ex is violent and poses a danger, but if your last breakup ended because you just were going in different directions, you don’t need to do a full disclosure on the first date.

Even harder to answer is how honest to be about parts of your life they might learn later that may be dealbreakers. I’ve been on a date or two before where I’m on the date, things are going well, and my date casually mentions her child or children. Now, at the time I definitely would not have dated a single parent (because I was 22 and 25 years old, respectively) but I don’t know if I think it’s inherently wrong not to bring this up. It’s true that many people find dating single parents to be a dealbreaker, but what if you don’t consider it a dealbreaker? Would you, or should you, disclose the fact that you’re a single parent to people before you go on a date with them? Honestly, I don’t know. It doesn’t put you at risk, but it’s also a big deal for a lot of people. Personally I’d prefer a disclosure before a date, but that’s just me. I’d much rather know if someone drinks or not before a date than whether or not they have kids, but I guess that speaks more to my dealbreakers than it does about anything else. The problem with dealbreakers is that we all have different dealbreakers, and you’ll never know what your dealbreakers are. The last person to ask me what my dealbreakers were, I think I said that one of them is the fact that I’m often perceived as cold, and that wasn’t a dealbreaker for her but my candor about dating was. While I’d prefer to meet and date women who live alone, it certainly would not be a dealbreaker for me if the person I’m dating lives with roommates, or even family, so I rarely if ever bring up my living situation. With that said, maybe if you’re a straight woman approaching her 31st birthday, you’d find a guy living with his parents to be a huge dealbreaker. What about employment, or underemployment? Should a person be obligated to tell you when they’re underemployed or unemployed? If you’re someone who never needs to work because of an inheritance, trust, or investments, do you need to disclose this before a first date? If you’re unemployed because you’re working solely on getting an advanced degree, when do you disclose this? I’m still on the fence and can’t come up with one clear answer that works in all situations other than simply being honest when you feel like the information is need to know. If you can afford dates because you inherited a ton of money from a rich uncle, I don’t think you need to disclose that until someone specifically asks what you do for a living. If you’ve got a child or children, whether or not you bring that up before, during, or after a date is up to you, because any of those times is fine. With that said, what you decide to disclose and when will be interpreted in different ways by different people, so even though you might be honest it doesn’t mean that it will negate whatever your dealbreaker might be.

Where I’ve landed is here: Complete honesty in dating, as in life, isn’t something most of us can do all of the time. Sometimes keeping it real goes wrong. I think that in order for the average dater to date honestly, they have to try to be as honest as they feel they should be at the time. If you’re going to choose not disclose something, you need to honestly feel as though it’s either not important now, or you’re not actively harming someone by not discussing it. You don’t need to go full-disclosure on every part of your life, just the parts that are important to know. Dealbreakers and risk factors are things that need to be disclosed, but there has to be some nuance in how you handle things. I think ultimately, if you’re honest with yourself when you ask if you’re doing the right thing with your disclosures, and lack of disclosures, you’re probably being as honest as you should be.

Complete honesty might not be the best policy, but being honest about whether or not your actions are harmful is as good as you can get.

Good Luck Out There.

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