Advice Column: Response to Clarify

Dear Hailey,

I was in a long term relationship, and we were engaged to be married. It’s been almost a year since I left my fiancé, which was one of the best/hardest decisions I’ve had to make, but I would have been miserable if I went through with it. I am just beginning to feel comfortable with the idea of dating again (though a bit rusty), and have been on and off talking to someone for about a month or two. 

I casually met him a few times (through a coworker) way before we started talking, so he’s not a stranger. I’ve noticed through our conversations that we have a lot in common and the same sense of humor, yet he’s still being strange when I try to ask questions to get to know him better. I asked how old he was (I’m guessing he’s within 5-6 years of my age) and he completely bypassed that (I asked again at a later date and still no answer). Then if I try to ask something different, he doesn’t reply, and I don’t hear from him for a week. It’s a pattern that I’m starting to see, but by certain things he says and jokes he makes, I’m 95% sure he’s interested in me. 

Full disclosure, we have a mutual friend that I messed around with many years ago, and I’m pretty sure he knows about it. I feel like that’s the reason why he’s unsure/keeping some distance. I was young and dumb at that time, and especially since my broken engagement, I am in a completely different headspace than I was when that happened. 

I was thinking of being direct and open about it so I can get some clarity, but I also don’t want to turn him off completely if I bring that up. I’m stuck as to how to read this situation and proceed. I’m not trying to force anything by any means, I just feel like I need clarification on what I should say (if anything).
Thanks in advance for your time and advice!


Dear Clarify,

First, I want to give you kudos on ending your previous engagement when you realized that it wasn’t the right path for you. It takes a lot of strength and courage to stop something that is already in motion, such as an engagement. Rejoining the dating pool after being in a committed relationship for a long time has its challenges. 

It’s absolutely understandable to have some red flags go up when you ask a direct question and he avoids answering. Especially when the question is something as simple (and essential to know in the context of dating) as age. I am not as concerned about this as I normally would be in an online situation, because you have met him and know that he’s not secretly a 53 year old woman, or anyone drastically different than what he has portrayed himself to be. 

I would absolutely recommend confronting/clarifying with him about how he avoids answering certain questions, and if the tension/avoidance present in your relationship is because of your previous fling with his friend. It will be better to know exactly what is going on, and it get it all out in the open. 

If clarifying something simple changes his feelings or the trajectory of your future relationship, it was not headed into a good place or solid to begin with. You do not have anything to lose by clarifying with him. 

Some recommendations on how to approach it:

“I’ve noticed that sometimes things seem weird or awkward between us, could it be because of my previous fling with Mutual Friend?”

“Sometimes I notice you avoid answering questions and then I don’t hear from you for a while after I ask about it. Is there a certain topic that is hard for you to talk about that you would like me to avoid in the future?”

Addressing concerns head on always feels uncomfortable in the moment, but ultimately will save you a from a multitude of concerns and heartache later. This means you can make the argument that in the long run, it’s actually easier to be direct. This conversation could give you the opportunity (if you would like) to share that you are in a much better headspace than you were a few years ago. 

I wish you luck,


Posted in Q&A

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