Dear Kylee:

The fact that you and him were friends for a year and were “open and joked around”- that is a good thing, it would have been nice if that openness and humor didn’t have to end because of the change of relationship status.

Clearly his “history he has had with in other relationships” is a concern of yours, as well as the fact that he is very friendly to other women while in relationship with you.

You were hesitant about being in a girlfriend/boyfriend relationship with him because “I become insecure whenever I get in a relationship. I have bad anxiety and over think everything. It stresses me out and prevents me from fully enjoying the relationship.”-

Bad anxiety is a condition that requires healing and/or adequate management. Anxiety predated this relationship, meaning he didn’t create it. He is also not going to solve it, or eliminate it for you. He can’t, no boyfriend can.

You wrote: “I have expressed to him how I have bad anxiety and its hard to deal with especially in a relationship. He listens and says he understands but I’m not so sure he does”- notice your motivation in telling him about your bad anxiety: is it so that he will help you with it? If so, how? Is it that he will be careful not to hurt you?

He told you that he “may come off miserable like or looking.. But that doesn’t mean he is… he’s not always the best communicator which leads to me overthinking things like oh he doesn’t care about me or I’m not enough for him..”- is it your tendency to think that when a person looks unhappy it means that you are not enough for him, that you did something wrong?

You asked: “Maybe I’m expecting to much? I just want to feel secure and confident when in a relationship and trust that things will work out how they are meant to”-

Of course you want “to feel secure and confident in a relationship”, that is, you wish you were not anxious. But you are. At times you may feel secure and confident but often enough, unfortunately, you don’t feel secure and confident. This is why my answer to whether you are expecting too much is: yes. Expecting “bad anxiety” which predated him to disappear in a relationship, is unrealistic.

Do your best to learn and evaluate the man you consider for a relationship: if his relationship history is realistically concerning and if he is flirtatious with other women while in relationship with you, maybe meeting different women alone for a drink after work, well, that is not a good candidate for any woman interested in a monogamous, long term, healthy relationship, anxious or not.

It will be helpful if you rely on logic to discern between his behaviors that distress you because of your anxiety alone (ex., him sometimes looking unhappy-  no boyfriend can look happy all the time), and what about his behavior is incongruent with a healthy, loving relationship (ex., if he gave you the “silent treatment” as a passive aggressive way to communicate with you his anger).

I hope you post again with your thoughts and feelings.

anita