I’m 28, never had a girlfriend and just got my first out of college job, how should I confess feelings to a lifelong friend?

[Anonymous]

I just wanna start by saying that this woman is beautiful beyond words, like she has MANY MANY options. I fear she won’t want an inexperienced virgin guy such as myself. That said, I’ve known her for fourteen years and finally developed true feelings for her 2 years ago.

When my father commit suicide at age 20, it sent me into a huge mental breakdown that took forever for me to recover properly. I finally went back to finish undergrad at 25, and graduated last spring. She never left my side even at my worst and I don’t think I ever will be able to repay her for that. There were days when she was my only friend in existence, this is why I love her so much now.

I don’t want to explain all this to her, it might be too much. All I want to know is how I can ask her out without risking ruining the friendship. I really love this woman, not just because of her beauty, but her nature.

[Ez-Bri-Z_v2]

That's tough because on one hand you obviously have feelings for her, but you didn't say if she's ever shown feelings beyond being a caring friend for you. Telling her might (and most likely will) make things awkward between you.

I guess there are some important things to follow up on. Is she already seeing someone? You said she has many options but not if she's already seeing/interested in someone. Being that close of a friend, that shouldn't be hard to obtain.

I wouldn't worry too much about being a virgin. Generally, we won't care too much about that. Just don't make it your whole personality.

[David5668]

Be honest and tell her, but have that reality check as well-she might not reciprocate your feelings. If that’s the case-don’t treat her like crap, be civil to her. Best of luck.

[Anonymous]

How do u look

[Asker]

Not horrible.

[Opinion Owner]

How do u both look? Height? Weight? Skin tone?

[Asker]

I don’t know her height, but I know she’s shorter than me.

I’m 5’ 9

[Asker]

Why does this matter?

[Opinion Owner]

It does.

[Asker]

I’m not the living reincarnation of Hercules, but I take care of myself and stay in shape.

[Opinion Owner]

How do u look? Your heights? How does she look

[IHateBeingaMan]

another reminder of oh well

[Anonymous]

I think this is more common in modern times