Ask John: My Boyfriend Has Baggage and More!

By John Siscel April 24, 2013 08:27 AM
0 COMMENTS     POST A COMMENT   Print This Post   Email This Post

Ask John: My Boyfriend Has Baggage and More!

Dear John,
My current boyfriend is super amazing. I really love him. He has a long history of relationships that weren’t the healthiest or ended really badly. I know because he’s told me about this. A lot
. Why is he sharing this?
– WTF?

Dear WTF,
It is probably one of two things. Either he’s trying to make sure this pattern doesn’t happen again with you or he’s afraid it is happening and he’s trying to prevent it. Maybe he hasn’t figured out what about this relationship is different and he’s trying to analyze it. Maybe he’s waiting for the other shoe to drop. Whatever it is, I see no point in him continuing to bring it up. Gently tell him that you appreciate the honesty, but there’s no point in continuing to talk about it. As they say, the past is the past and it’s time to shut the door on it. If he can’t, and you notice that he frequently expresses himself as the victim in the past relationships and you see a bitterness growing, then maybe you need to suggest a therapist for him to process these residual feelings. Someone who can help him resolve these issues and move on.


Dear John,
I’ve got this really great guy friend. He’s funny, sweet, shy, kind, and…I’m in love with him. Not in a friend way. I didn’t know this until I broke up with the last guy I dated (who was a totally jerk, by the way). How do I tell my friend that I want to be more than that?
– Nervous

Dear Nervous,
First off, relax. Your guy friend has probably entertained romantic notions about you at least once during the friendship. If he’s a “nice guy” he may have been trying to get with you but wound up in the dreaded “friend zone.” At any rate, converting your “boy friend” into a “boyfriend” is a lot easier than you think.

Here’s what you do: take him out for a drink. Make sure it’s just the two of you. Chat a little bit, relax, make sure everyone’s comfortable. Then state it clearly say “Hey, I want to put something out on the table here. You can take it or leave it. I’m going to go the bathroom after I say what I need to and when I can return you can either take me up on this offer or pretend it never happened and we can move along as always. But I have deep romantic feelings for you, and I’ve finally realized it. I want you to be my boyfriend and be your girlfriend.”

That’s not the whole speech, but enough to get you started. Basically lay it out in no uncertain terms. Be very specific and clear and present it as an offer. Then as I said, get up and use the restroom, make a quick support call to your bff, whatever and then come back and see what his response is. He’s probably been waiting for this moment and won’t let you leave the table. If he says yes then you’ve got a great adventure in front of your. If he says no, have no fear. I promise you, there’s nothing like knowing something for sure to give your heart a way to move on. If he tells you, ”I don’t feel that way about you, I actually like someone else,” hopefully he’ll be a good enough friend to ask what he can do to help you. And you can say, “Just be my friend.” You will move on.