I have many female close friends, but never goes beyond friendship

[JohnGoober]

 have many female friends, including women my age and single moms. The majority of my close friends are female, although I do have male friends from my childhood. I feel more comfortable around women, and we engage in activities together such as going to movies, taking vacations, attending opera shows, hiking, and going for walks. We do pretty much everything that couples would do, except we are just friends. I currently live in a shared house with a few housemates. A girl moved in a few weeks ago, and she doesn't really talk to anyone else, but she talks to me. She even asked me to move out with her to a better place. With most women, I genuinely just want to be friends. However, when I see someone as a potential girlfriend or date, I can't be myself around them and end up putting them on a pedestal. I enjoy paying for meals, taking them out, and giving small gifts based on their preferences, even when they are not my girlfriend. If they feel uncomfortable, I let them pay. I also treat my male friends who are close to me by paying for them as well.

The problem is that I never communicate my intentions if I want to ask them on a date, nor do I make my intentions clear, hoping that they will make the first move (in every relationship I've been in, the woman has made the first move). I have also missed out on reading hints, even when they got drunk and confessed their love for me. What I fear the most is ruining the friendship or facing rejection. I believe that men and women can just be friends, but most of the time, the friendship fades away because they enter into a relationship. I'm also extremely afraid of being the "second" choice. In my first relationship, I was the "backup." She had been cheating for over a year, having sex with a guy who was fun to be with, while I was the stable boyfriend. My best friend also kept me as a backup, only reaching out when they didn't have anything else to do or always canceling plans at the last moment. I have always felt like I'm not important in anyone's life.
I do have low self-esteem, and my overall happiness depends on getting validation from others. For example, when someone I like contacts me, my mood becomes happier. I know this is dangerous, but I don't know how to address this issue. I do feel sad when they don't reach out to me, but I make sure I never contact them too much. Regardless of whether I feel sad or not, I never try to make them uncomfortable because I know there is something deeply wrong with me.

A few weeks ago, I met a girl through a hiking group. Although we barely talked the first time, I ran into her a few weeks later near my home, and it turned out that we live just 5 minutes away from each other. Although I didn't ask for her number, we had a nice conversation. We met again during a hiking event, and this time, we got to know each other better. At the end of the hike, she gave me her number and asked me to call her. She mentioned that I was the first person she befriended because she felt she could trust me.

Initially, she was excited to make plans with me. We started hanging out, watching movies, having dinner, just the two of us. She tells me that she doesn't normally do these activities because they drain her, but she feels comfortable doing them with me. Every time we meet, she gives me my favorite chocolates or snacks, and I do the same for her. She even calls me by nicknames and insists on buying me dinner. Once, when I didn't text her for a couple of days, she asked me if she was important to me or not, but then told me she was just joking. Ironically, she doesn't really text me often, even though when she's with me, she responds to her friends' messages frequently. I don't expect her to like me, but it hurt a little when I realized I'm not important enough to her. However, ever since our last meeting, I feel like she has lost interest in me. I took her out to a concert and dinner, and we walked together very late at night. I didn't make any moves because I asked her to "hang out" instead of calling it a date. She was also able to sense that I was a bit insecure and nervous around her (which I often feel when I like someone). I felt like she may have been interested in more than friendship in the beginning, but not so much anymore. She does talk about her ex-boyfriend every now and then, probably not completely over him. She told me that relationships are too time-consuming and draining, and she loves the freedom of being single. However, she also mentioned that if the right guy comes along and she feels comfortable around him, she would consider getting into a relationship. I'm not sure if she's trying to test me, but she keeps teasing me about wanting to date her roommate, who is single. She also keeps telling me she would look for someone to set me up with. I rejected these offers because I want her to know I'm not interested in anyone else. I'm wondering if I have already screwed up my chances with her.
I know I need to stop giving off friendly vibes and make my intentions clear, develop my own personality, and be more assertive, but I don't have a clue about how to go about this. I wait too long to see if they like me, but by then, it's too late.

 

 

[Weezy1973]

8 minutes ago, JohnGoober said:

I know I need to stop giving off friendly vibes and make my intentions clear, develop my own personality, and be more assertive, but I don't have a clue about how to go about this.

The core problem is your low self-esteem and low self-worth. Are you in therapy? If not, that would be my first suggestion. Everything else you’re talking about stems from that. 
 

Practically speaking, you need to be okay with rejection. Someone rejecting you doesn’t mean you’re a bad person, or that you’re not worthy of being loved, it just means you’re not the one for them. Some women will find you attractive and some won’t, just like you find some women to be attractive and not others. 
 

So with this particular woman, you should let her know how you feel. If she doesn’t se you “that way” that’s fine, you at least have an answer. And then she can set you up with her friends!

[Wiseman2]

2 hours ago, JohnGoober said:

 She told me that relationships are too time-consuming and draining, and she loves the freedom of being single. 

This particular woman is not interested or ready willing and able to date at this time.

Why not get a good profile and pics on quality dating apps and start talking to and meeting women? This makes it clear that you're looking for dates, not friends.

It's fine to have friends, but you seem to wish you had a GF but are heavily overinvesting in being in the male-girlfriend zone rather than investing time and energy into searching for women to date.

Keep in mind, unavailable people choose other unavailable people. So reflect on why you're spending all this time with taken or uninterested women.  

[glows]

I think you’re reading into things. Just pop the question if she’d like to go on a date and flirt with her. See if she returns the same vibe. She already teases you and you have a good rapport.

You say she senses you’re insecure and nervous and for all she knows you’re the one who isn’t attracted to her or for whatever reason you don’t see her as dating potential. Enjoy the moment. If you’re that close as friends or “get” each other and she doesn’t see you that way, laugh this off! Don’t let it affect you so much.

It’s great you’re going out and meeting new folks.

Edited June 9, 2023 by glows

[Versacehottie]

4 hours ago, Weezy1973 said:

The core problem is your low self-esteem and low self-worth. Are you in therapy? If not, that would be my first suggestion. Everything else you’re talking about stems from that.

This is exactly it. I think if you don't deal with this any progress you make with this specific hiking group woman would be temporary. 

OP, I think it's ok that you treat once in a while in a "friends" situation but if you are paying for people or overly giving toward them, it's unbalanced and typically results in people losing respect for you. You need it where they are VALUING you! Where they are putting you on a pedestal in some way to try to gain access into your life. I think subconsciously or unconsciously if you do too much or pay for things excessively, people know you are trying to "buy" your way in and your worth actually goes DOWN in their eyes....Because it begs the question: "if he's so great, why would he need to buy his way in?"  Especially if you are going out of your way (financially or giving of your time/effort). That's normal(ish) if you are dating someone  but not when you're not.  Don't be the guy people take advantage of because then you won't be able to get what you really want.

Edited June 9, 2023 by Versacehottie

[smackie9]

I'm not one for this but here goes....you are in your predicament because you have low masculine energy. You will forever be in the friends zone unless you makes some changes in your social life, habits, lifestyle, etc. Sucks but there it is. 

[Lotsgoingon]

You need to fine tune your approach.  I recommend therapy---with a woman therapist.

If you don't want to do therapy (which really wouldn't take all that long) then you need to open up about this very struggle with some of your women friends. If you are really friends, you should be telling these women buddies about your dating struggles and asking for help. A good woman friend will help you. Heck, ask one of those friends to go to a social event with you and let her coach you on approaching people and let her notice what you're doing and not doing. 

Right now you're people pleasing. You're working way too hard even as a friend. With my close friends, heck we can go for a walk in the park and have a good time. I zoom with them and make phone calls. I don't buy any gifts other than treat them for a birthday brunch once a year. All the gift giving is getting in the way of real intimacy, even friendship intimacy.  You're actually hiding behind all the niceness and gift giving.  With a friend, you don't walk around thinking of a gift for them. Your friendship is the gift! There is no greater gift! Literally. There is no greater gift than just being a friend, which mostly involves talking every now and then. The trust, the laughs, the support in difficult times--that's a treasure. Way better than all the outings and gift giving that you're engaging in. Real friendship does not require all that effort.  

What you are missing is your own body awareness. On a date, you tune into your body. Are you feeling joy? Not just intellectually that this person is a good person. But do you feel pleasure? You feel the other person's interest. You notice how close they get to your space and how close you enter their space. The body language is different on a date than a meetup with a friend. You smile more, for example and an interested other person smiles more at you. You also dress differently for a date than for a meetup with a friend. I'm totally comfortable looking like a bum with my women friends. I spiff up for dates. 

You need to kill friendship as a backup goal. You come to a meet with a dating interest with a goal of seeing if you want to go out again as a date. If you don't feel a connection, you don't shift to friendship. I mean, you can do that but only 1 out of 100 times. A date doesn't go well, at the end you say "it was nice meeting." And you go your separate ways. 

But if you've got women friends, ask them for help! Otherwise, they aren't really friends! 

 

 

 

 

Edited June 9, 2023 by Lotsgoingon