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No dating experience. How do you know if a friend is interested?


RockmanX

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I need advice.

 

I'm a 39 year old male and one of those 'never dated never had sex' people. I've fallen for a woman (37) I've been friends with for 2 years now and this is one of those times I truly regret being socially awkward all my life. Without going into detail, she has recently bared her soul to me about her relationship issues. She only had 1 real relationship in her life and essentially is lonely.

 

Is this her way to try to get me to ask her out or just trying to get comfort from a friend (which of course, is what I did in the moment)? A large part of me feels I should just ask her out and just to hell with the outcome. I've never done this before and that fear of so many different things holds me back. We've had long conversations several times in the past, she is always quick to point out similarities and things we have in common, shows me her old pictures, we lean on each other for moral support, talks about her ex (I think I remind her of the good qualities about him)etc.

 

Like I said, I'm clueless about this .

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A woman who is ready to pursue a new relationship would not speak about her ex(es) or talk about her relationship woes. If your red flags are going up, there's a reason. I'd hold any idea of pursuing a relationship with her unless you are certain she doesn't have any screws loose.

 

If you want to date her or have sex with her, just ask her out but I wouldn't consider her relationship material if she's still hung up about her exes.

 

Can you be more specific about what your fears are?

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My red flags are up from fear. I'm overthinking and overanazlying everything.

 

I have had nothing but terrible experiences since I was a child with the opposite sex. I'm fine talking and making friends until I realize I caught feelings, that's when the awkwardness kicks in and I never act on it and just suppressed my feelings out of fear. I was always morbidly obese most of my life and failing time and time again at even getting a job did a number on my confidence and self esteem, but that's changed. I've lost an absurd amount of weight (still fat, but it doesn't really bother me as much because I'm always dropping weight) and I've gone to great lengths to rid myself of anxiety by attacking things that scared me or made me feel uncomfortable.

 

It's certainly boosted my confidence and made me escape a negative thinking cycle, but just letting someone know that I like them? All those insecurities just come flooding back ten fold at the very thought of letting someone know that I like them. It's way easier to do public speaking several times.

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My red flags are up from fear. I'm overthinking and overanazlying everything.

 

I have had nothing but terrible experiences since I was a child with the opposite sex. I'm fine talking and making friends until I realize I caught feelings, that's when the awkwardness kicks in and I never act on it and just suppressed my feelings out of fear. I was always morbidly obese most of my life and failing time and time again at even getting a job did a number on my confidence and self esteem, but that's changed. I've lost an absurd amount of weight (still fat, but it doesn't really bother me as much because I'm always dropping weight) and I've gone to great lengths to rid myself of anxiety by attacking things that scared me or made me feel uncomfortable.

 

It's certainly boosted my confidence and made me escape a negative thinking cycle, but just letting someone know that I like them? All those insecurities just come flooding back ten fold at the very thought of letting someone know that I like them. It's way easier to do public speaking several times.

 

If it's causing you this much trouble and anxiety, I wouldn't do it. I don't think you're ready to let someone in and please don't take this as a derogatory remark or something all bad. There's always room for improvement with everyone. If you're experiencing this much trouble right now, I cannot see you being happy with yourself in a relationship either. You're already having trouble accepting yourself and have trouble with self-esteem.

 

It's really up to you how you want to live your life. This person may be just friendly towards you and not interested in you in the least. You'll have to be self-confident enough to not let that get to you if it happens to be the case. Are you able to handle the possibility of rejection or not having the same feelings reciprocated?

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Well, first of all huge congratulations on losing the weight! As a bigger girl myself I know how difficult it can be. I understand being awkward regarding dating too. I've been there myself.

 

If you're just overweight and not obese anymore, some people don't mind that. I don't mind and I've dated many overweight people, even at times when I'd trimmed down myself. A romantic connection is not always about body size, it can be a lot more. It's hard to know if this woman likes you or not, but don't you think it's time you stopped always being in the friend zone? I think you should just go for it and ask her out. If she says no, that's OK. There are a lot more women out there.

 

Also to put things in perspective for you, everyone gets rejected. My best friend is very pretty, slim, nice and has a successful career. A lot of guys are into her, but she gets rejected too. It's a normal part of life.

 

If you never even try then how can you succeed? If you want a relationship (which it sounds like you do), why don't you try to go out and get it? It's your time to shine now! Good luck!!

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I know for a fact life is short and wasting opportunities and worrying until you've killed it, is no good.

 

Just ask.

 

Sage perspective there...

 

In my own life I don’t regret any rejections I’ve had. I don’t regret my marriage or any other relationship I’ve had. I do look back and wish I had gone for it, like really GONE for it, more often.... Good luck!

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Hey RockmanX, you're overthinking it! You don't have to do some grand gesture or official "will you go on a date with me?"

 

Literally just ask her if she wants to go to get a drink and food with you. We're talking super casual and what you'd do with her as a friend, but also - assuming you two are having fun - after the night is over tell her you had fun and ask if she'd want to go out again with you.

 

Be open and flirtatious, don't feel you need to hide the fact that she's cute; but you should allow yourself to develop your feelings with her to know if this is someone you want to see, and you do that by doing these first few casual dates.

 

Dating is not supposed to be strenuous, it's supposed to be fun; so approach the first ones as they are supposed to be: basically a friendly night out and seeing if she wants to do it more regularly with you ... but put a little flirt into it, nothing overt; but compliment her if she looks nice; before you split for the night, tell her you enjoy seeing her and would like to again, etc.

 

The first few dates are friendly, not crazy romantic ; don't over analyse or think the old hat stuff is required... forget the fancy, expensive restaurant and forget the wild flair of romantic gestures, etc. That comes later if you two connect well

 

The first few dates, you're hanging out with her and seeing if you two actually have chemistry. Avoid the talk about pasts in so far as relationships. Focus on you two there and now and have fun - ask her questions, listen to her stories and return reciprocate with your own. Hold a damn good conversation and at the end of the night, try to pick up the tab; if she wants to go dutch, that's fine!

 

You're putting far too much cart-before-horse by focusing on a "relationship" - that comes much later. Right now it's seeing if you two can even have a true crushy-friendship for the first few dates... and you'll see that IF you two do have chemistry after a few fun dates, the next parts come pretty naturally once the first part there starts clicking with someone ... since you're basically now comfortably talking to your friend, except both of you have this whole other thing for each other. Relationships are built over time, not started.

 

Worst thing that would happen is she'll politely tell you she doesn't see you like that but hey, you'll have gotten some dates under your belt and know what to do for the next person and not have this kind of over-expectation on what these first few dates really are.

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Stop making friends / being friends with people if you are interested in more.

 

I don’t think this girl after two years is looking for more than friendship from you.

 

Perhaps it’s time to stop being her sounding board and ask her advice on dating?

 

Tell her you are interested in dating and ask her how she would advise you to go about it?

 

Stop being her friend and let her be yours.

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OP,

I'm 10 years younger, but I can kind of relate. I think it's pretty bold of you to come on here and tell us about your inexperience with women, some people don't fess up to that so easily.

 

Look, as everyone else here has said... if you like her, just ask her out, quit beating around the bush. Look, in the past... I was like you. Very inexperienced with women and dating. Now starting to get drastically past the anxieties of approaching and asking them out and have dated a few women now. I've learned that dating... it's a really complicated thing. It takes time to get to know people, to get to build relationships with them. Intimacy and sex is complicated! You may really like this woman now, or be interested. But after spending some time with her in the romantic sense, you might not click. And that's life.

 

So for that reason... just get past your anxieties and ask her out. You're never going to learn about her, or learn about yourself, by sitting around doing nothing. You'r way overthinking and over-analyzing things, and you're not getting any younger. Just ask her out, if she's not interested, move on with your life and look for someone else. I'm telling you man, listen to the others here, listen to me. You're wasting time on thoughts and fantasies, thinking about "what ifs".

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Thank you all for the replies.

 

I've fallen into something of a depression over this since my last response. It's like all the progress from weeks of therapy and self confidence were just flushed down the toilet and I'm just beating myself up over this and back to the same negative thinking cycles. All I can think about is that kids more than half my age have more experience with even just hanging out with people they like and my own inability to express myself just hurts.

 

I didn't plan on liking this woman, I actually kinda hated her when we first met and thought she was annoying. It's funny how that works. There is a part of me that just wants to go meet other people and I try to find every excuse not to move forward (I'm much taller, heavier, different races, no experience, different hobbies ,etc) but I have to do this for myself and just ask her out. Whatever happens, happens.

 

I do have another question though. Why would anyone be so terrified to let someone know they like them? I'm sure she suspects I'm into her, but me letting her know that? That just terrifies me for some reason, it always has. Like I said in the OP, she shares some emotional baggage with me that is pretty severe and hurts her to the core and I'm always just fighting back the urge to comfort her and suppressing my own feelings to her. The couple of times I couldn't suppress my emotions any longer were beautiful moments where we fully embraced with a long hug, but the next time I ran into her I'm terrified and acting aloof.

 

But like I said, I'm going forward. I don't know what I'll say but it'll be brief and sincere.

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I do have another question though. Why would anyone be so terrified to let someone know they like them? I'm sure she suspects I'm into her, but me letting her know that? That just terrifies me for some reason, it always has. Like I said in the OP, she shares some emotional baggage with me that is pretty severe and hurts her to the core and I'm always just fighting back the urge to comfort her and suppressing my own feelings to her. The couple of times I couldn't suppress my emotions any longer were beautiful moments where we fully embraced with a long hug, but the next time I ran into her I'm terrified and acting aloof.

 

 

What is terrifying you is that you don’t know how you will deal with rejection IF she rejects you.

 

She might not suspect you are interested in her because by your own admission you suppress your emotions.

 

She might feel cheated if she truly thinks of you as a platonic friend but suddenly you let her know you have feelings for her and therefore in her eyes an ulterior motive and not exactly the friendship she thought she had.

 

The friendship you describe does sound a little one sided , as in she vents and you listen.

Does she ever listen to you? What do you get out of this friendship?

That’s why I suggested you talk about yourself and your interest in dating , see how she responds??

 

What does your therapist have to say about this? I’m sure you asked in therapy before coming to a forum?

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When you allow yourself to open up to someone, you then become vulnerable to being hurt. That's for anyone, not just you.

 

And it can be extremely daunting. But it's a part of dating and having a relationship.

You have to put your heart on the line and hope and pray that it goes alright.

 

Sometimes it does and sometimes it doesn't. I think those of us who have dated can say we have 100% had our heart broken at one time or another.

The good news is...it's survivable. And as much as it hurts at the time, the pain goes away eventually.

 

Work on being okay with whatever possibility that may come along.

Life has no guarantees. But that shouldn't make us stop living or stop trying to find love.

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I'm much taller, heavier, different races, no experience, different hobbies ,etc

 

Dude, none of that matters - NONE OF IT; this isn't about the things you don't have in common - it's about the things you do have in common and seeing if she is interested. I've dated plenty of people who have different hobbies and almost all were slimmer and shorter than me - as many women are.

 

Also, give me a break, if race is a factor for either of you then you need to get your heads screwed back on correctly because I've dated people of many "races" and I promise you, everyone - to the person - is just another human being sharing the same sliver of time we have together on this planet.

 

As for experience; you have experience with women - this woman here literally sees you as such a comforting presence that she confides in you and hugs you for the piece of mind you provide to her ... I know guys who for the life of them can't comfort someone when it actually counts; THAT is inexperience. This woman might not be "the one" but I promise you, there is a woman out there who would F*ing kill to have a partner with the amount of emotional support and empathy you seem to be able to muster; but before she can get you, you need to overcome your fears and emotional roadblocks, so do her (whomever she is out there... ) a favor.

 

If you mean you don't have sexual experience:

 

1. You're putting cart far, far before horse. We're gearing up for the first date here, it won't end with sex or anything remotely close. Relax.

 

2. I'll let the ladies on this board confirm/deny - but if you think just because other men have had a lot of sex that they are all experienced in how to do it; I've heard from plenty a good source that you're dead wrong.

 

Stop creating reasons why it wouldn't work and just ask her out to dinner and drinks. Maybe it will work out or maybe she only wants this to be platonic. If it works out, cool. If she wants this to be platonic, you're a gentleman so you'll let her know you understand and respect her wishes; regardless, you will have finally done it and realized the world kept spinning.

 

Also, again, stop thinking this is some weirdly formal "will you go out with me and begin to be my partner in a relationship" question. That's not what a first date is! That's not what any date is! Relationships happen they aren't forced.

 

It's a "Hey, would you like to grab dinner and a couple drinks with me sometime" question. A first date is literally just hanging out with someone you think is fun no kissing, no sex, none of that... just fun conversations over drinks and some food - if it seems like you both have a lot in common after that, ask her if she'd like to do it again a few days later and go have fun again, and again ... like I said, the romantic part happens naturally during dates; your only job should be on just having fun together when you both go out. Nothing forced or expected from either side.

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You need to try to look at it for what it is supposed to be; it's literally just getting some food and drinks with someone you're interested in. I know it feels like it is something more significant, but it's not.

 

I'd actually suggest it might be smartest to go onto a dating app, hit it off with a few strangers and once you know you two have something in common; ask them if they want to get a drink. Meet them, pretend in your head like you've known them for years and just treat it like meeting a friend and learn something new about someone and share stories/outlooks/opinions/etc. The first dates are not anything more significant than that.

 

Getting a few "first dates" under your belt will get you to relax a bit about it; and once you've been on a few and find someone you think is interesting, the second date is literally the same as the first but now you'll just be more comfortable with the person so there's even less feeling of awkwardness... then the third date even less... then you two just naturally go with the flow and the 'intimate' aspects develop organically .. That's why it seems so effortless for other people who are 'experienced' as you put it, it's because it is pretty effortless once you start doing it and stop putting "dating" on a nerve-wracking pedestal when reality is you're just getting a bite to eat and a couple drinks with someone else, or going bowling, or [insert activity].

 

You'll get the hang of it, just got to get over this first hurdle and a whole new world will open up for you.

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The dating app comes up often. I suppose it's a good idea for practice but I honestly don't have any interest spending time with people I don't know.

 

But yeah, passing that initial hurdle is my problem. I had my chance a couple of hours ago and blew it but I'll try again next time I see her.

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You're spending what seems like a lot of thought and energy to find reasons NOT to date.

 

If you expended that much effort into actually dating I think your experience would be different. Maybe not a whole lot, maybe a LOT, but different.

 

Like they say, if it's important to you you'll find a way, if it's not important to you you'll find an excuse.

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