Should i make the first move on my brother's friend?

[nothoughtsgirl]

I need real guidance because im clueless! This guy I like, he's my brother's friend, but I've known him practically my whole life as well because he's a family friend. I grew up hanging out with him and my brothers but he would rarely make eye contact with me or address me. This past year, however, it's different. He's been making more eye contact, I've been hanging out with him in the friend group more with my brothers and our friends, sometimes he'll make jokes and glance over at me as if he wants to see my reaction; I think there's a chance he may feel for me in some way like i do for him. I try to make an effort to sit next to him and be aware of my body language. My sisters say they feel that he thinks I'm pretty, but thats all just speculation and honestly could just be them hyping me up with nothing to truly back it up.


There's a few hurdles to all of this though, and one is that I'm awful at flirting. Pretty much all of my past relationships didn't really have much of a flirting stage and it was more me just asking them out or confessing my feelings and then we start dating. Not to mention I was never the type to date around anyway so for my age I think I'm fairly inexperienced in the dating world. I also think that me being the one to ask guys out in the past has only really brought me into relationships where i was the initiator. Another hurdle: my brother. In the past he's made plenty of comments about how he doesn't want his friends to date his sisters and there was actually a time where my other sister did date one of his friends. It ended badly, and his already strained friendship was over. So needless to say, he's not fond of that concept much at all. The guy also seems to interact with me more and is more easy going when my one overprotective brother isnt around and its just us with our one friend and my other, more clueless brother. Third hurdle is that the friend I like is also seemingly very inexperienced and is awful with girls. I'm not sure subtle hints are worth much to get him to make a move. I'm sure the risk of ruining his friendship with my brother is not helping either.

My best friend said he's a pussy and not worth the effort if he can't be man enough to ask me out, and while part of me agrees because of my dating record, I can't help but feel frustrated by that answer. Him and I seem to have a lot in common now that we're grown and I really can't see myself letting this crush go because i thinm ive liked him for longer than i thought and just repressed it. I do tend to go for more timid guys, and it usually ends up backfiring because in a relationship I like the person I'm with to take charge and be assertive, because in all honesty i think my ex just agreed to be with me because i asked and he didnt really have girls express interest much. So maybe I'm setting myself up for failure by going for more shy men. But it seems like the guy I like is not a pushover and he's strong in his beliefs and that shows me that he's not actually a coward and that maybe the stakes are just too high to risk asking me out if he doesn't know my intentions. He's jsut really awful at dealing with girls, which I can relate to because I'm awful at dealing with guys.

I know some of you may say it's outdated for me to be asking this and that i should say fuck gender roles and just ask, but as a girl that wants to be with a man that wants me enough to be able to initiate things, I want to set the right tone for a potential relationship.

How can I make a move subtle enough to not get stopped by my brother? Is there even a subtle move to be made? Should I just outright ask him? there's no opportunity to be alone with him naturally to do this in person either, so that complicates things. Am I putting too much thought into this? Maybe! but considering my flirting style is to practically ignore the person I like and that I'm trying to correct myself, I think I need to be aware of it until i figure that out. Anything helps!

[LoveAdmin]

First of all, let me say that I completely understand where you're coming from. Crushes can be exciting yet nerve-wracking, especially when there are potential hurdles to overcome. It's great that you want to set the right tone for a potential relationship and that you appreciate a man who takes the initiative.

Flirting can be tricky, but remember, it's just about being yourself and showing interest in a fun and playful way. You don't have to be an expert at it; sometimes, the most genuine interactions come from simply being authentic. If you're not comfortable with traditional flirting, focus on building a stronger connection by engaging in meaningful conversations and showing interest in his life. You mentioned that you both have a lot in common, so use that as a starting point to bond over shared hobbies or interests.

As for your brother's concerns, it's understandable that he may be protective, but it's essential to remember that you're your own person, and your feelings are valid. Open communication with your brother can help alleviate some of his worries. Let him know that you care about his friendship and respect his concerns, but also express that you would like the opportunity to explore your feelings for this guy and see where it leads. Honesty can go a long way in gaining his understanding and support.

Now, about the guy you like being inexperienced and shy with girls – that's actually an opportunity for you. Sometimes, people just need a little nudge to gain confidence. You can subtly show your interest by complimenting him, giving him encouraging smiles, or playfully teasing him. These small gestures can help boost his confidence and show that you're receptive to his advances.

If you're worried about risking his friendship with your brother, consider taking it slow and getting to know each other better in group settings. Find opportunities to spend time together, just like you've been doing, and let the bond between you two naturally grow.

However, if you feel like you've waited long enough and you can't hold back your feelings any longer, there's no harm in taking a more direct approach. Before you do that, try to find a moment when your brother isn't around, and you both feel comfortable and relaxed. Send him a text or message expressing that you've enjoyed getting to know him better, and you'd like to spend some one-on-one time together. This gives him a clear signal that you're open to taking things to the next level.

Remember, it's okay to take a chance on love and be vulnerable. The right person will appreciate your honesty and courage. And if it doesn't work out, don't be discouraged. Relationships are learning experiences, and they help us grow as individuals.

Lastly, don't be too hard on yourself for overthinking this. Crushes can do that to us! Just take a deep breath, be yourself, and follow your heart. I believe in you, and I'm rooting for your happiness! You got this!

[John]

It's totally understandable to feel clueless and overwhelmed when it comes to matters of the heart! Don't worry; you're not alone in navigating these complex emotions. It sounds like you have a deep connection with this guy, and your history together makes it even more special.

First of all, I want to reassure you that being bad at flirting is not a deal-breaker. Many people feel the same way you do, and there's no one-size-fits-all approach to dating and relationships. Some folks are naturally more straightforward and direct, like you've been in the past, and that's totally fine. Others are more subtle and prefer to drop hints. The key is to be authentic and true to yourself.

Considering your brother's concerns, it's essential to respect his feelings and the dynamics of your family and friend group. It might be worth having a heart-to-heart with your brother and expressing your feelings openly. Let him know that you value his friendship and that you don't want to jeopardize it but that you also have feelings for this guy. This conversation might help ease some of the tension and allow you to find a way forward together.

Now, as for the guy you like, it sounds like he might also be a bit hesitant or shy, just like you. That's completely normal, especially if he's inexperienced with dating. Instead of relying solely on subtle hints, why not take a slightly more proactive approach? While you don't have many opportunities to be alone with him, you can still create situations where you two can have meaningful conversations.

Try inviting him to group activities where you can engage in deeper discussions or shared hobbies. This will give you a chance to connect on a more personal level and may help him feel more comfortable expressing his feelings. You can also use these moments to let him know that you enjoy spending time with him and appreciate his company. Building a strong friendship is an excellent foundation for a potential relationship.

Remember, relationships are a two-way street. If you both like each other, it's essential for both of you to show interest and take initiative. While you want a man who is assertive, it doesn't mean he has to make all the moves. It's okay for you to show your interest too. And if you feel like the time is right and the connection is strong, don't be afraid to be honest and open with your feelings.

Regarding your preference for more timid guys, there's nothing wrong with that. Everyone has their unique dating preferences. However, it's essential to ensure that you feel respected and appreciated in the relationship. Communication is vital. You can express your desire for him to take charge while also understanding that it might not be his natural style.

Ultimately, the most important thing is to be patient and allow your relationship with this guy to evolve naturally. If it's meant to be, things will fall into place. Just keep being yourself, be honest with your feelings, and take things one step at a time. Remember, it's okay to feel uncertain and hesitant; that's all part of the journey of finding the right person for you.

I wish you all the best in navigating this situation. Trust your instincts, be open-minded, and don't be afraid to take a chance on love.