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Hard to Say is This Recording’s weekly advice column. It will appear every Wednesday until the Earth perishes in a fiery blaze, or until North West turns 40. Get no-nonsense answers to all of your most pressing questions by writing to justhardtosay@gmail.com or by dropping us a note at our tumblr.

Hi,

We have all heard the maxim, "Once a cheater, always a cheater." I have been dating my boyfriend David for over a year. Early on in our relationship, when we were not exclusive, he explained that he had also been seeing another girl, who we will call Serena. He told me that he was going to break it off with her and that was that.

Recently he told me he had plans to meet up with Serena again, and reassured me that it was only in a friendly context. Initially I had no problem with this, but my curiosity led me into a google rabbit hole and I viewed Serena's online presence in its entirety. She is a very, very attractive presence, in a lot of ways that I am not. For example, she has long blonde hair and a tiny waist.

When I brought this up to David, he again told me there was nothing to it and said all the right things. He offered to cancel, but I said it was OK. Now I am kind of worried though. Objectively I don't believe he ever cheated on me, but I can't help having that feeling in the back of my mind. What should I do?

Denise F.

Dear Denise,

If your relationship was strong and committed, the reappearance of Serena should not have a negative impact on what you share with your beau. If it was strong and committed, she would just be a faceless woman that was once a part of his past and now is not.

Speaking to the situation at hand though, you have two options: You can demand to be there when he meets up with her. You can make your presence known. You can publicly establish the boundaries to her. But all that does is shine a negative light on you. It makes you seem paranoid. If I was Serena, I would think that there’s something wrong within the relationship. And there’s no point in giving this other woman the upper hand by showing your cards of insecurity.

Instead, the best option is to ask David the nature of his past relationship. Was Serena just a woman he was dating casually at the same time he began to date you? What defines casually? And how long were they together? You can ask these questions in a to-the-point manner. It might seem confrontational (because it is), but it is better than worrying yourself over something that you ultimately can’t control. Be honest with how this makes you feel to him. Get it all out in the open, ask for honesty in his response, and trust that the strength of your relationship will provide a sufficient enough answer.

Hey,

I am a 20 year college graduate who takes medication for my bipolar disorder. When I inform my dates of my condition or that I take regular medication, they do not react very well. Usually in their eyes I see a fight or flight response reminiscent of a young doe. When is the right time and manner in which to bring up my condition?

Nathan R.

Dear Nathan,

There is no set time when it might be appropriate to share sensitive information, but you will probably know when it’s right. Usually the other person will have shown you that it is okay to say these things, normally by sharing their own stories. This could be on the second date or in the second month.  Dating allows both people to test the waters. As the relationship grows, so should each person’s trust in the other. If you pull somebody into the deep end with you right away, you won’t know if they’re up to it. They haven’t earned your trust yet, and you haven’t earned theirs. Start small, like with a bowl of pistachios.   

It’s also possible that you are dating people who aren’t ready to be in real relationships. If you’re still rebuffed even when you’ve waited until it’s natural or necessary to share, then move on and don’t blame yourself. They are the ones who need to grow up.

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