Decision time

Alright then this time it is kind of like a vote, so at the same time as I have been talking to you guys I have been talking to another one of my female friends and I have only just realised now that as I have been talking to her I have been getting closer to her as we have been talking more and spending more time together as well.

I am just wondering should I go and ask her out straight away or take my time, I am just wondering as when I usually wait I wait too long. What should I do?

Jason, if I read you correctly you are asking if we think you should ask her out. It has been some time since I practiced this kind of thing but from what I have learned,

Do NOT ask her out now.
Think of little ways you can spend time together that are not intimidating.
Do things that involve her saying yes but do not constitute a date like say staying for an afternoon event at school and walking her home.
Working on homework at her house.
Talking on phone and getting comfortable.
meeting her parents so you can see if they are reasonable human beings for her as well as you to deal with. If they know you, then that may be easier to get to going on a date.

When should you try a formal date? A lot depends on things we cannot know.

If anyone tells you to go on the date right away, that is the easiest way to lose a friend.

Thank you so much for the help and you do have a great point losing her as a friend is the last thing that I would want.

Also I was wondering should I draw the line at flirting or should I flirt with her?

All of these questions are hard to answer without being the person in the situation directly, especially with the "should I flirt " thing.

Thing is the best gauge for what to do in any given situation with another person especially one you are considering getting involved with romantically is to get to know them and discern the best course of action based on their behaviors, yours and a whole slew of things that only you and she will know.

Although there is no set standard for what is right or wrong when courting someone with the goal of a romantic connection at some point, going slow is almost always the best approach. People forget much of the time when they rush into romance that in a relationship the best basis is actually being friends first and letting the romance grow, because romance, passion and emotions come and go but the one thing that should be consistent is a close friendship. that's what will make the relationship last in the long run.

As for flirting again getting back to interpreting and understanding her actions, ask yourself if she seems open to flirting and if you're comfortable with it, some light flirting is a good test to see how she handles it, whether rejecting it or accepting it.

But overall focus on the more important things like friendship first. it doesn't have to be the end goal, but it's one that is fundamental.

Hope this helps.

*added note*

btw if it's someone that's interested in you, likely you can never wait "too long"

Thank you so much for the help and sorry for all the questions I am bad at these types of things.

aw no don't apologize. asking questions is never a bad thing.

I'm glad I could be of help.