Date With Best Girl Friend

Been friends with girl for a long time.

When we met she had just gotten out of a 5 year relationship.

She had a one year relationship after that.

She told me pretty early that she thought I was cute and that she liked me a lot but nothing ever came of it (at the time) because of her getting over her relationship - where many things when wrong - and we were at different points in our lives. I continued to date and so did she.

Long story short, we decided we wanted to start dating.

Couple of things we are worried about. Breaking (physical) intimacy barrier.

She is a "tomboy" and has A LOT of guy friends. I am FULLY secure in myself and am not worried per say but she is worried as her ex got really jealous even though he said he wouldn't.

We are really close, she shares things with me that she has only shared with her brother who is her best friend.

On the one had the situation is extremely exciting but on the other it seems a little awkward and I feel and I cannot "operate" it in the same manner as an random floozie I would meet at a club.

Anyone go though something similar and have advice on how to make the transition?



Most Helpful Girl

  • Awe! It's like when Barney dates Robin from How I Met Your Mother! Okay, I'm done! First off, I think it's great that you're willing to make this work and it's clear you care a lot about her and taking a mature angle. Very important stuff. Quite honestly, it's just treating her how you treat her now with sweet gestures. Just take it slow with intimacy and test the waters as you go. Breaking the friend barrier is hard to work on and rushing things could make it awkward. As for the psycho ex, tough cookies for him. Hope everything works out for you!


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What Girls Said 2

  • BE CAREFUL if it doesn't work out it could go from something great to very awful quick. Take things slow and test the waters, but I would see how things play out otherwise you'll never know

  • Gosh, I am in a situation that so closely resembles this that it is almost scary. Number one thing that stuck out to me in this question is the mention of the ex. I too just got off of a five year relationship, and when you are with someone that long, they still sort of stay with you even if you are no longer in a relationship. Ultimately, I found that my ex was an anchor weighing me down. You struggle to move forward if you haven't fully let go of the past. Obviously, you cannot tell your friend (girlfriend? potential girlfriend?) how to handle this, but I found that diminishing my contact with my ex was the best way to go. It was hard at firs, but it helped me to move on and pursue new men.


What Guys Said 1

  • Your relationship has a great potential of working out.

    Simply be true to yourself, be more confident, and start spending a lot of time with her.

    Take her out to dates. Pay compliments a lot.