Oscar is in love with his newly single best friend, how should he tell her and approach the situation?

Please help me…PLEASE! I’m not some high schooler looking for help. I love this girl, she’s perfect in every way…she just broke up with her boyfriend 2 days ago. We were best friends before we messed around once, we didn’t have s** but we messed around. I stopped talking to her because I liked her and she had a bf. I love this girl, I can see myself marrying her. We hung out the last 2 days. I took her out for food today just hanging out. What should I do? I want her before she picks another guy. I’m a lil over weight though but not horrible. Guys hit on her like crazy too but we were best friends so we do hang out

– Oscar


Hi Oscar,

Thank you for submitting your question in such detail.

Before I say anything, let’s leave you being “overweight” out of this issue, unless it matters to her? You’re saying you’ve been her best friend for some time and you’ve even had some intimate moments with her in the past, so your appearance obviously didn’t matter to her. She must have found you attractive in some way or another, so let’s leave that out of this issue.

Now the real problem is…

The fact she just broke up with her boyfriend 2 days ago, and you’re already wanting to make her fall in love with you.

It is sweet that you love her so much and how you’re being there for her and everything, however, wanting her to fall in love with you right now seems like an unrealistic desire to me.

I’m not saying it will never happen, but you wanting it to happen right now, definitely doesn’t sound right.


In Love with my Best FriendBecause right now her emotional state could tempt her to fall for you and even claim to fall in love with you, but, there is a damn 99% chance that she’s going to use you as her rebound. Since you were already a good friend of hers, she could use you as her rebound until she is over her ex-boyfriend and simply end it with a “Sorry, we can still be friends” with you.

Yes, I know I sound so negative, but you really have to think from all sides.

That’s how most of us are to be honest. When we break up with our boyfriend or girlfriend, we are often left with so much depression and loneliness that causes us to seek attention from someone else. It could happen to this girl too and you don’t want to be used as a temporary replacement do you?

So what the hell do I do?

Continue to be a good friend to her and be there for her. Help her to recover from her ex in a friendly way without rushing her into anything. Even if she gives you positive signals in the beginning, it probably won’t last long if she decides to date you right now. So you really have to be patient with her.

You yourself are saying “I want her before she picks another guy.”

See what does that say to you? Obviously she’s not mentally mature enough to choose her perfect partner at the moment. Right now, she could fall for literally anyone, just to get over her ex-boyfriend. And I really don’t think you should fall prey for that since you actually love her so much.

Be her good friend that you are and just give her some time to recover first. Wait at least a few months and see how she has progressed from her ex before you start giving her any dating signals.

SEE ALSO: She said “I’m not ready for a relationship yet. What do I do?