Note: This letter was edited for clarity.

Dear Dr. Deb,

I’m 57 years old, happy, and confident with myself and my life. But I’m in the middle of a murky situation that leaves me feeling like a confused teenager.

I’ve been seeing this guy casually. Or at least, I think I am.

We started off as friends. At the time, we were both trapped in horrible relationships. We confided in each other, and this made us closer.

After our respective relationships ended, we started hooking up. He shows signs of interest in me, and it seemed like he wanted to get more serious with our relationship. But just when I thought we were going somewhere, he pulled away. I didn’t stop him and gave him space.

Lately, we started talking again. It’s been going well, seemingly getting back on track. But then he started sending me videos of people ending their relationships and joking about having commitment issues. It felt like a passive aggressive way to pull away from me again.

Dr. Deb, how do I know for sure what he means by this? What do I do about his hot-cold actions?

Sincerely,
At A Loss

Transitioning from being just friends to hooking up can be exciting, awkward, and confusing, all at the same time.

While friendships are a strong basis for romantic relationships — some of the best love stories start out this way – it seems like you both bonded over your dysfunctional relationships, but very little else. Romantic relationships become fulfilling when they include genuine friend-based intimacy, trust, support and closeness. 

Maybe you and your “guy friend” have a fuller sense of each other than your letter implies. But something’s not right because some time after hooking up, he’s suddenly left you out in the cold, and is now acting strangely, in a passive aggressive way.

The simplest answer is often the correct one: he’s showing all the signs of getting cold feet after hooking up.

You need to take a step back and look at how it started. Were you both ready and willing to move from being friends into lovers? I know you’re on board, but is he? His hot-cold actions would say otherwise.

Realizing that you and your friend have the hots for each other can be a lovely experience that might lead to true love. However, whether you like it or not, Ms. At A Loss, sex can change things. It makes your relationship more emotionally complex than your friendship ever was.

In fact, you need to admit that this is no longer your usual hooking up situation – you’re seeking a deeper, romantic relationship with him.

Can people go from being just friends to dating to actually having a successful relationship?  Of course they can. “Losing” your friend by becoming partners is worth the risk, but only if you both want the same thing.

You mentioned you share a history of bad relationships. It’s worth taking the time to understand what went wrong with your respective situations. Take responsibility for your mistakes, reflect on the reasons, and figure out how you can do better in the future. If you don’t, you will repeat them over and over and over.

You might think you know your friend like the back of your hand, but dating him is guaranteed to reveal his different side. And maybe this is his “real” side that you’ve never seen before.

To get answers once and for all, you need to be honest with yourself and consider: maybe what he wants is just not what you were hoping for.

Yours,
Dr. Deb