Dear Joey:

When do you think is the best time to give a potential boyfriend bad news?

Say you have to tell him you’re bipolar, or that you have an STD, that you’re on parole, or that you’ve have gender reassignment surgery. (Or something!)

Do you tell him before he gets to know you so that if he rejects you it doesn’t hurt as much and you didn’t waste as much time?

Or do you wait until you guys know each other better and then he may like you more and be less likely to reject you based on only a single piece of information?

I mean, for 2 of those scenarios, obviously you need to tell them before you have sex, but in general, is there a point at which it’s either too soon and not soon enough?

Potential Girlfriend

Dear Potential:

Great question!

Before I get in to what my thoughts are (your miles may vary) – I want to first point out that you have two different sets of information detailed here: things you’ve done, and things you are.

Things you’ve done that may be affecting you now are potentially bad news that may reflect negatively against you. In your examples, I would put the parole part right up there. The STD might fall there as well, depending on how you contracted it.

Things you are would definitely include being bipolar and being transgender. For the record, I would not count either of these as “bad news” – just facts. You are who you are are.

But I understand this is Earth, not Utopia, and people may react differently to you once they know these things. So instead of “bad news” – I think we need to discuss these as potential dealbreakers.

That being said, I wish there was a mathematical formula I could give on when the right time is to talk about stuff that could be troublesome, but there currently just isn’t. (I’m sure someone is trying to work on the algorithm, but for now we are just going to have to muddle through this.)

The Golden Rule of “do unto others” comes to mind. When would you want someone to tell you?

I tend to like the 3 date rule as a general baseline. Typically, the third date is symbolic for when you get more intimate with someone. The first date you are nervous and just trying to see if you get along. The second date you are checking out if this potential chemistry is a fluke, or if the lack of chemistry was due to nerves. By the third date, you are starting to see that this is going somewhere, but instead of just making this a physical mile-marker, make it a true intimacy moment and talk about who you are beyond liking baseball and thinking Kirk is better than Picard (or vice versa).

Things like the STD has a medical impact on your potential partner – you need to discuss it before sex, like you said. And if you are pre-op Transgender, that might be a bit of a surprise if you don’t discuss it before the clothes come off.

Any medical condition: being bipolar, having cancer, being allergic to bees – these are things you need to discuss if you are going to be in position where people around you may have to react. If you are going to spend the night or the weekend with someone, they need to understand that you have medication that you have to take, that you have appointments you have to go to, that you have an epi pen in purse.

But in reality, timing is something you have to figure out for yourself. What impact will revealing these things about you have on your ability to date? Is not telling someone going to prevent you from being yourself on a date because you are afraid of rejection? Then go ahead and get it out of the way – it may seem “too soon” to other people, but you are not other people – and you have to do what’s best for you. If someone will run after hearing that, it gets it out of the way.

As for other bad stuff in your past, like having gone through bankruptcy, or being a former nun or drug addict – I say, take that as it affects the relationship. This might not need to come up by the third date, but it definitely needs to be addressed before the 90 day rule – especially if the relationship has gone past casual dating to something potentially long term.

Again, just think about when you would want someone to tell you those things and use your best judgment. And remember that who you are is never bad news –it just might not be the right fit for someone unworthy of you.

Wishing you love and happiness –


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