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Advice for When You Feel Too Insecure To Date

Advice for When You Feel Too Insecure To Date

Advice for When You Feel Too Insecure To Date

Tips on What Your Insecurities in Your Relationship Could Be Telling You

Advice Seeker :
Dear April Masini,

I've been with my boyfriend for about a year now, but I've known him since we were little kids. All through high school, he had various girlfriends and I was never on his radar at all. I was a chunky little thing who never dated in high school. I went to the prom with my best friend and had no romantic interests at all. I know he dated a lot of girls in college, too, and I heard a lot of drama went on in his relationships. He cheated on a few of his girlfriends, used them for sex, and just seemed kind of like a jerk.

However, when we reconnected last year, we really hit it off and started dating. I was amazed that he actually liked me and found me attractive (I'm still amazed!). Throughout the whole relationship I've been a little insecure, mostly because of the stories I've heard about him. I've also caught him in a few uncomfortable situations- I saw on his Myspace that he was talking about sex with girls. When I confronted him, he said it was no big deal and that it was something we could "add" to our relationship. He tried to get me to talk about my sexual past and told me a lot about his- stuff I didn't want to hear! But I pretended to be really interested and even asked him a lot of questions because I know he really wanted to tell me. Now he talks about his past sex life with all the time and I don't know how to tell him it bothers me so I just go along with it.

I'm starting to get really uncomfortable in this relationship and don't know what to do. I need some it time for me to break up with him? How would I do this?

Sincerely, Sick and Tired


April Masini's Advice :

Dear Sick and Tired,

You already know what I'm going to tell you. You're not ready for a relationship. You've got to work on yourself and your self esteem before you can feel comfortable in a relationship. You don't really like this guy you're with and have been wasting your time. You called him a whore in your letter to me. That isn't what someone calls a man that they love.

If you're angry at him for having a past, then at least acknowledge that and allow that maybe this isn't the right guy for you for now. But more likely, I think that you're angry at yourself and your own past. You refer to yourself as "a chunky little thing" as a child, and you mention going to your prom with your best friend -- not a romantic date. If you're comparing yourself to him, you may be angry that he had a lot of sex and relationships and you didn't. You may be lashing out at him, when you are really angry at yourself.

Either way, you need to take some time off from dating. This habit the two of you have of talking about sex acts with other people that you were involved with and what you did is bound to hurt feelings, and the fact that you keep doing it even though it's hurting you, is of concern. Why would you want to hurt yourself or allow him to hurt you unless you felt that you deserved to be hurt?

Your own discomfort with this whole situation is a bright red flashing light that is telling you what to do, but you're not listening to yourself, so let me help you hear your inner voice:

Break up with this guy without any drama. Just tell him you had a great time, but you want to move on. I can assure you that this guy is not going to make it easy for you to move on. He's going to keep coming after you for sex and affection -- and he's going to be going after other women, too. You'll be vulnerable, so you have to support yourself by reading Think & Date Like A Man, and surrounding yourself with good friends and family who have your best interests at heart.

After you buy and read Think & Date Like A Man, write me and tell me how it's going. I'm so sure that you'll do the right thing and find someone, after you do your own work, who loves and respects you as well as himself, and would never ask you what you did with other men, or tell you what he did with other women if it makes you so uncomfortable. And as for his communicating with other women he had sex with on MySpace -- don't waste your time with this guy. He's not committed in a healthy way to you. You deserve better. You'll get better.