On the first date especially, but also on the few after, it’s important to be on your best behavior, to put your best self forward. Yes, you want to be yourself, but think: best version of yourself, not: you at your most emotionally honest. It’s not being dishonest, it’s just being smart. If all goes well and you begin to date regularly, you’ll have plenty of time to show them your ugly side, trust me! Being too comfortable and too raw right from the start is a red flag of emotional instability, lack of awareness, and lack of courtesy. However, I know It can be difficult to know what’s appropriate to bring up on the first handful of dates, and what’s not. So I have put together some guidelines to follow.

Definitely mention :

If you have ever been married

For most reasonable adults this should not be a deal breaker. In fact, if anything I think it makes you more interesting. But regardless, if you were married previously your date has the right to know. I suggest bringing it up no later than the second date. You just don’t want it to turn into a thing later, like something you were trying to hide. When you mention it, I recommend also volunteering how long the marriage lasted, as well as how many years you’ve been apart (divorced and separated). I would also be prepared to objectively summarize why you feel the marriage didn’t work (some examples: “we grew apart,” “they changed a lot,” “we were very young and it was a mistake”), and (as a bonus) what you learned from it (divorce is terrible but hopefully for your sake you got a learning experience out of it at least). I also encourage you to ask the other person if they have any questions. This shows that you are open, ready to move on, and have nothing to hide. I would avoid (in these first several dates at least) trash talking your ex (this makes it seem like you are not ready to move on), as well as praising your ex too much (same reason).

And if you are still married and live with your spouse, then stay home!

If you have any children

I’m not being funny here, I know of people who for months didn’t know that the person they were dating had a kid. They kept it from them as though it was a dirty secret, which is really disrespectful to your kid (or kids) as well as the person you’re dating. I realize it’s hard sometimes to share information you fear may result in the other person not wanting to be with you, but wouldn’t you rather know if the other person is not cool with kids? In most cases, the other person is okay with kids, just not okay with lying about it or concealing it. And if they’re not okay with kids, do you really want to be with them anyway? If you have a child (or children), mention it on the first date. You need to know they’re okay with it before there is even a date two.

Probably mention :

If you have a chronic illness

For these purposes, I would define a chronic illness as a health condition that currently affects your daily life. This is a tricky one. It varies person to person, situation to situation. I admit that it’s not something I have much experience with, but I think it’s better for you to mention it sooner than later. My advice would be to focus on having fun on the first date, but I think by the third date at the latest you should mention it. If your disclosure of a chronic health condition scares someone off, then they are not the right person for you anyway.  You don’t want to waste your time.

Optional, but you can mention :

Death of someone in your immediate family or someone else you’re close with

This is only if you feel emotionally ready, like you can mention it without sobbing uncontrollably. You don’t HAVE to mention it, but if you’re able to talk about it while staying in control, it can be a nice way to express your vulnerability and connect with the other person.

Mention, but don’t talk about it for too long :

Your career

Most people are interested in hearing about their date’s career, but not the entire time. Try to balance your side of the conversation with questions for the other person, and about the things going on in your life.  If you find yourself constantly talking about your work and career (on dates, to friends, family, your pharmacist, etc), maybe that’s a sign that you need some more balance in your life. It doesn’t have to be anything crazy, it can be interests that are easy to fit into your busy schedule, like reading novels or watching Netflix. Bottom line – mention your work, but have other things to talk about as well, and ask the other person questions about themselves!

Don’t mention :

If they look like or remind you of someone

Save that kind of thing for later on. You never know if a comparison will offend someone, so just keep that to yourself for now. On a second date, my friend was told that she looked like a certain porn star her date likes to watch. Do you think there was a third date? Nope! Which leads me to…


Personally, I don’t think there is anything wrong with watching adult porn in moderation (I know there are some who disagree), but bringing up your porn watching habits or sharing your porn collection on the first handful of dates is a red flag to others that porn takes up way too much of your time…and energy.

Fond memories of your ex

Just don’t, especially during the first handful of dates.  There were obviously good times with your ex or you wouldn’t have been with them, but don’t share this with your date. I guarantee you that even if they don’t indicate this, it will make them feel like shit and they will dwell on it and angrily bring it up later on in the relationship.

What you didn’t like about your ex

The older we get, the more likely we are to have an ex. I believe that part of getting to know someone is sharing your history, and so it is acceptable to discuss your past relationships eventually.  However, I believe it’s wise to avoid going into too much detail, or bad mouthing them, on the first few dates.

Your sex life and other TMI

A friend of mine told a story of how she agreed to get set up on a date with a man twice her age (she was 30, he was 60). Going into it with an open mind, she was repulsed that on the first date he said to her, “don’t worry, I take Cialis.” She thought that was a crass and presumptuous thing for him to say on the first date, and I agree. After a while you can discuss your bodily functions, or medications that affect them, but not on the first date, or even the first three dates. Even if you have sex at some point during the first handful of dates, keep your sexual function medications and other TMI to yourself. Allow some mystery. Your date probably also doesn’t want to know about other people you are currently sleeping with (unless one of those people has an STD).

Oh and speaking of STD’s, always wear a condom until you are monogamous and you and your sexual partner have had a full STD panel of tests from a doctor and have shared the results with each other. You’d be amazed how many people do not do this, and wind up with HPV, Chlamydia, or worse. You’re welcome!

Thanks for reading! Anything you think should belong on these lists that wasn’t mentioned, or something mentioned that you disagree with? Tell me in the comments!

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