How do I progress a newly formed friendship into a romantic relationship?

Question

I am 27 and don't have any experience dating. My problem is that I have been totally an introvert for the past 10 years, especially with girls, so I don't have much experience when it comes to girls. Recently I am trying to fix this by getting in touch with some friends or even finding new friends, specifically girls.

The hitch is that my first try happened out of my control (the whole thing got initiated by her), by a girl I really like. I fear getting stuck in the friend-zone or someone snatching her away. I understand that I can't control these things, but I don't want to express my feelings too soon, as the last time I did that I just ended up in the friend-zone from the very beginning. I also lack the experience so I can't even tell if she might be into me or not, whether she likes me, or when would be the right time to tell her how I feel. It is worth mentioning while I have these insecurities and lack of experience, she has lots of friends that are boys/men and spends so much of her time socializing with these friends. I can accept that she has lots of friends that are men in theory, but it still is so hard to wrap my head around it in reality.

Also note she is really special to me. I understand and respect her freedom in choosing friends, also the fact that she is free to eventually choose whether to give me a chance, keep the relationship as friends, or cut all ties with me.

So knowing most of what my problems are, how can I progress the relationship, not so fast that she gets spooked or backs out? And if possible, how can I tell if she might like me or she might give me a chance?

The friendship is now 2 months old, although I knew her for a year. We go the same university. She is about to graduate, and although she studies hard and has much better grades than I do, I helped her lately some of her courses and exams.

Edit: I have to note I am from and live in Iran. Also another aspect of the problem is that playing video games and watching certain movies has made me sort of an over-thinker. I overthink almost everything and also try to plan my moves ahead, so as to be prepared for every situation, which actually works exactly opposite of what I expect it to. Either I don't take action due to the overthinking, or I try to plan things which are completely out of my control and instead ruin everything. Note that this relationship itself was part of the improvements I made, so I am trying to let go of my destructive habits.

Answer 1

There are a couple things I want to clear up before I get into your main question of how to progress the friendship into a romantic relationship.

First off, being introverted simply means you find interacting with people to be draining and you need some time to yourself to recharge after a lot of socializing. It does not mean you are incapable of or dislike socializing. Many introverts have excellent social skills and deep friendships. This may seem pedantic, but I say this to shift how you view yourself: maybe socializing is difficult or tiring for you, but it's still a skill you can develop like any other. So don't let that label hold you back. It sounds like you're already taking some great first steps, so well done!

Second, the infamous "friend zone" trap. Do not buy into this. People look for different things in romantic partners than they do in friends, so naturally there are people that any given person would happily be friends with but not date. It's not because that person did anything wrong, it's generally just a romantic incompatibility thing. Think about your male friends who you truly value. Would you date them? I'm guessing not, right? And that has nothing to do with them not being good enough or them saying the wrong thing or anything like that. You simply aren't interested in them romantically due to something outside of both of your control. Even if one of them is harboring a secret crush on you, you haven't "friend-zoned" them. You are just being their friend and have no romantic interest in them. And that's totally fine, because that's what being a friend is.

Okay, with that out of the way, let's get to your main question: how can you progress this friendship to a romantic relationship? How do you know if she'll go for it? For better or for worse, the answer to both is the same: ask her out and see what she says. It's possible she'll say no. There's no way to know for sure she'll say yes before you ask. There are signs you can look for, but it's not foolproof. Some people flirt with everyone regardless of interest, some people are shy and never flirt even when they are interested. You can't know for sure unless you ask. So ask her! If you don't ask, then you're telling yourself no. It may feel like a huge risk, but really the worst case scenario is you're still in the same situation you are right now. A rejection may bruise your ego, but you'll be fine, I promise. I've been turned down before, I've turned people down before, it's only a big deal if you make it one.

If you'd like to remain friends even if she's not interested in you romantically, then I'd explicitly say that when you ask her out. If not, then just don't mention it. If she turns you down, don't stay her friend if your only motivation for doing so is because you hope you can change her mind. That's typically what people really mean when they say they've been "friend-zoned": someone attempts to demonstrate they're worth dating by being a great friend and then complain when they stay friends. This approach doesn't work. Be friends if you want, don't if you don't, but don't act like you want to be friends if you're only interested in being lovers. It's dishonest and disrespectful.

Good luck!

Answer 2

Every person is different, and every romantic relationship is different. But in general, it's always in your best interest to be open, direct, and honest. Tell her "I'm afraid of messing up our friendship, but I've developed romantic feelings for you" --because that's the plain and unvarnished truth. Whatever decision she makes at that point, she'll be able to make it knowing the complete story. And whatever happens from there, you'll know you'll have at least taken positive action. (Also, if she's the one that initiated your friendship, it means, at the least, that she sees you as an appealing friend. And who knows, perhaps she's interested too.)

As a side note, you should probably try to expand your social circle a little more, no matter what. It's a bit of a red flag that you've fallen for your first real female friend --is it really this specific person you're in love with, or just the fact of relating directly to someone female? And even if she is interested in being your girlfriend, it would be a lot of pressure to be both your girlfriend and your only close friend. If you have other good friends, and outside interests, you'll find her other friends less threatening. Making friends with her friends, or at least being friendly, isn't a bad idea either. Maybe they aren't your competition after all.

I don't know if this is appropriate for your culture, but in my culture (USA) it is usually considered a good idea to do a lot of casual dating --just meaning going on dates with different people. That gets you more comfortable with (potentially) romantic situations, allows you to consider a wider range of possible futures, and makes it so you are less destroyed by rejection or heartbreak.