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I’m Dating My Ex Boyfriend’s Brother

Dear Andreus,

Roughly ten years ago I used to live in NY. While there, I dated this exceptionally nice guy, and the only reason it ended, was because I relocated to Florida for work.  Recently I started dating a guy here, and after a couple months, he asked me to go to brunch with him, his brother and his friends. To my amazement, when we arrived at brunch, the guy he introduced me to as his brother, is the guy I was dating in NY. I knew that there was something familiar about his features, but I would not have thought of that in a million years. My former boyfriend pulled me aside and told me not to say anything, because he feels like his brother doesn’t really need to know.  I feel like I should say something, because honesty is very important to me. Should I keep silent?


Jarrell K.

Dear Jarrell,

What are the odds?  But I suppose stranger things have happened. I always stick beside the belief that honesty is the best policy. Though bringing it up may be awkward or uncomfortable, it is probably best said then found out accidently later. The truth always has a way of surfacing, especially when you have been given the opportunity to share it and did not. Clearly none of this was intentional, so there is no need to feel guilt or shame, just tell him. If he finds out later and knows that you and his brother kept your past a secret from him, that might be more catastrophic.  Get it all out, so that hopefully you can continue without any dark shadows. 

Dear Andreus,

After three months of dating this amazing man, I am overcome with emotions. We have so much in common, but he is different enough to keep me intrigued. It has been a long time since I have had this connection with someone, and I want to express how I feel. Lately, I have found myself on the verge of telling him that I love him, but I don’t want to mess everything up by saying it too soon, especially if he is not on the same level, or ready to hear it. When do I know that it is the right time?


Mark G.

Dear Mark,

First let me say that I am very happy for you. As for your question, this is an age-old dilemma. When is it the right time to say? “I love you.” Clearly the biggest fear behind this is rejection.  But also, the fear of saying it too soon, or not soon enough. There is no perfect or exact moment, and if things are going well, then don’t rush it. He will make clear his feelings, and I believe that you will know when it feels right. With love, there are always risks, and getting it right means that you’ll just have to take those risks. Feel him out, and don’t be afraid to ask him how he feels about you. Look for clues and allow it to happen organically. I wish you two all the happiness in the world! 

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