Get Back Together with My Ex?

Dear Elana,

Some time ago, I started dating this amazing guy. Everything was great and we got along in every way. However, he had finished a two-year relationship right before we started dating, and after a few months he said he wasn’t ready. We concluded that probably not enough time had passed since his previous relationship, and that he could not be emotionally available to me or anyone else. My heart was broken, but as we both really liked and admired each other, we decided to stay friends. Now we spend time together, but I am still in love with him. How do I know if he is ready for a relationship? When that happens, how can I make him see me as a romantic interest once again? P.S. We are gay. Thank you so much!

– Hopeful Underdog Not Giving Up


It sounds like the first question is how honest your friend is being with you. Is he really “not ready” to be in a relationship, or is he hesitant about being in a relationship with you? If you truly believe that your former flame can keep burning, then you need to have a conversation. Ask him how he feels about his ex, and how he feels about you. Remind him of the fun you’ve had together, and tell him you want to keep having adventures with him. However, I would caution you to examine your expectations. It is possible that he will remain your friend, but fall for someone else. If that time comes, make sure that you are open to other matches whose flames are burning brighter for you. 

Help! I'm In Love With My (unavailable) Best Friend

Question: I have this problem and I need your help. I'm in love with my best guy friend. I have known him for over a year, and we're so close we tell each other everything, but he has a girlfriend. We work together in an office where we often work late, and sometimes he sleeps at my place. Lately he has tried to make out with me,  but I refuse. I know he likes me as a friend, but maybe he feels the same way about me? What can I do? How can I know if he has feelings for me?

Answer: I get it. You're falling in love with your best friend. You spend every day together at work sharing intimate thoughts and feelings, and the secrecy is intoxicating. It's exhilarating, and you can't stop wondering if it's meant to be. 

It probably hurts when you see him with his girlfriend, or when he is unavailable because he is with her. You’re confused because you don’t know if you should bare your heart and tell him how you feel, or respect his relationship and back away.

Here's the thing: if he's already comfortable cozying up to you at night, your feelings for him are hardly an unsolved mystery. The truth is, he could end his relationship and pursue you, but he isn’t budging. He seems content cheating on his girlfriend, and leading you on in the meantime.

Next, think about how your actions could hurt his girlfriend. How would she feel if she found out that you are allowing her boyfriend to spend the night at your house? 

I have to believe that you are reaching out to me because deep down you know that you deserve better. You deserve a man who will make you a priority and will move mountains to be with you. You are worthy of requited love.  

In psychological terms, you are operating from a scarcity mentality: you are willing to pursue a man who is taken because you believe that eligible men are in limited supply. In reality, there is no shortage of single men. There are plenty of smart, funny, dashing men, but you are oblivious to them because of your infatuation with your unavailable guy friend.

This beau of yours is getting his emotional needs met without offering you anything tangible. My advice? Expect more. Research shows that when you expect more from a relationship, you get more. Embrace an abundance mentality. Open your eyes, get dressed up, go to an art gallery, chat up a stranger, cheer at a baseball game, and when you catch the eye of a handsome gent, make sure to raise your standards for character before getting attached. 

Despite all my warnings, if you can’t imagine moving on without an answer – proceed with caution. 

Tell him that it hurts to be just friends because your feelings for him are deep. Listen carefully to his response and accept his answer. If he says that he shares your passion, tell him that he needs to end his relationship before he can be with you. You can celebrate, but don’t be surprised if you find him sneaking around with another woman behind your back. If he chooses to stay with his girlfriend, then you will likely need to stop socializing with him until you can tolerate being in his life without being intimately involved. In that case, focus your attention on meeting someone new, someone honest, loyal, and unattached.