Worried about his history

We chat at 1 p.m.

I have never been in a serious relationship before, unlike my close friend "Anna." Recently, one of Anna's friends took an interest in me.

At first I was cautious because there's a bit of age gap, and it seemed he'd just gotten out of a very serious relationship a month ago. I confided in Anna, telling her my concerns. During our conversation, she told me that they were intimate two years ago but that it never led to anything more.

Now I have no idea what to do. We have a connection, but when they are together, they do too, even though they don't know or acknowledge it. Anna has had a boyfriend for a year, but I still can't help but worry. I don't know what to do or how fast or far to take this relationship, or if it should even happen. Please help.

– Not Anna


Do not assume that Anna and this man have been longing for each other for two years. They didn't couple up when they could have. He's interested in you, and Anna has a boyfriend.

My guess is that Anna told you about their time together because you asked about his history – and because she didn't want you to find out from someone else. That doesn't mean the information is important. I have to wonder whether you noticed this "connection" between the two of them before you knew they had history.

The bigger concern is that he's newly out of a relationship, but there's not much you can do about that. Your best bet is to spend some time alone with him and see how it feels. If you like him, you can explain that you don't want a fling.

I know you want guarantees that your first relationship will be both serious and perfect, but it doesn't work that way. All you can do is try.

– Meredith

Readers? Should she be worried about Anna?