‘He told me he was never her boyfriend’

We had a broken comments section for a bit yesterday, so please make sure you give some advice to yesterday's letter writer.

I matched with this guy on two dating sites and we decided to go out on a date. Our first date was amazing! We went to a restaurant and were just so caught up with each other. Constant eye contact and light hand touching ... it was fab. Then he offers to drive me home because he was going to visit his friend who lives near me. Turns out this friend of his is someone I know – because I was intimate with him years ago. I decided to tell my date because communication is key. He admits to me that he had sexual relations with a friend of mine as well. Side note: She told me after this that he was her ex-boyfriend! I was shocked because he told me on the date that they just had sexual relations and nothing more. She said that they dated for a couple of months. He told me he was never her boyfriend.

Since then we have been intimate and we've hung out at his place a couple of times and he was really sweet and affectionate. The second time that we went out to eat, however, he wasn't being affectionate at all, and when we were walking and saw his coworkers, he turned the corner to dodge them. He told me he avoided them because they were co-workers he doesn't like, but I'm not sure if he just doesn't want to be seen with me. My question is: When is the right time to ask where we are in the relationship or what we're doing? I don't want to say it too soon and sabotage any chance of a relationship, but I also don't want to wait and get played for an extended period of time, like he did to my friend. My friend, by the way, said she'll be OK if I date him.

– Complicated and Confused

Wow. What a small world. I'm surprised you hadn't met this man before.

Even though there's a lot of history here, let's try to focus on the present. If you're at the point where you'd like to invest more time and get to know this man better, you can ask him if he’s on the same page. Make it clear that you're not expecting a betrothal or anything. All you want to know is how he views this relationship at the moment. You can explain your concern about the miscommunication with your friend. If you're spending time with him because you're hoping for more, you'd like to know he's open to that, too.

Exclusivity can be part of the conversation. If he's seeing others – or trying to – that puts things in perspective. It doesn't mean you have to drop him, but you'll know to keep your eyes open. He's not your everything just yet.

Also, I guess I’ll give him the benefit of the doubt about those co-workers. If it happens again – or if he declines to bring you around any other person in his life – that's a problem. But I think we've all done complicated moves to avoid people we don't want to see. It happens.

– Meredith

Readers? Is it too early to get a relationship status update, based on what happened with the friend?