I asked a guy out for my friend to try to get her out of her shell. Was I wrong?

[Anonymous]

My friend is such a beautiful girl with a warm, wonderful, colorful and vibrant personality. Every time I bring her around the single men I know, they always ask why she’s single at 40. I think the reason is because she’s a hermit who refuses to come out of her shell, and she seems to like being in her shell also. She came to me asking for help with talking to people as she’s in sales and has a monthly quota of how many sales she makes in a month. If she doesn’t meet the minimum, she’ll get fired, and she reported that she was struggling. Outside of work, she doesn’t go out, won’t meet men even for a one night stand (she claims she’s demisexual, which means no sex until she forms a bond). I think this is a big part of why she’s single. She won’t go on dates and refuses to have sex. She’s been going on more dates (because I’m a meddler and I love to matchmake, and because I’ve been sticking my foot up her ass to get her into a healthy, happy relationship), but WILL NOT BUDGE FOR THE LIFE OF HER about having sex (even though there’s no point dating if you’re not going to have sex).

She was talking to a man she met on hinge recently and told him she thought he was cute (which I told her “good girl”). I told her to ask him out but she won’t because she refuses to get with the times and actually ask someone out and instead waits for the guy to ask her (outdated dating practice that I don’t do and that I tell all my single girlfriends to nix). To me that sounds like an excuse to stay in her little bubble. I know she would be more successful I dating if she was willing to be the pursuer and I’ve made it my mission to get this girl a man whether she wants one or not, so she tells me she’s talking to this guy, I ask her to show me a pic. She taps on the app and hands me the phone. I take it from her and ask the guy out for drinks from her phone. He accepts and tells her all the stuff he wants to do to her on the date, she blocks him and gets pissed at me.

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I can’t believe she’s upset. She’s not going on dates, meeting men or getting laid and I think all three would increase her social skills and her confidence, which would then boost her performance at work as she would
become more confident and credible in her sales pitch, which would boost her sales quota. Yes, I’m being pushy and using it as an excuse ti match make her and get her laid, but I’m doing it to help her. Am I wrong? She’s a stunner with an amazing heart and a wonderful personality

[Finchie40]

I know you are her friend and you care about her , but unfortunately only she can make her decisions non what she chooses to do , by you intervening into her dating life is sadly going to make her resent you for stepping on her toes. I know you mean well but unfortunately only you are best to stop and let her make her own decisions, Once you back off of her and focus on yourself , she will eventually feel like she is missing out on things and hopefully start dating again. I dealt with the same thing , when my brother and his wife divorced , he went through a depression and didn’t date anyone for 5 years , i was always on his case about getting out there and meeting girls’ but it went it one ear out the other , to the point I gave up trying to encourage him. When he would call me or text me , I would say I will call you later , I am out on a date , once he realized I was going out and having fun , he decided to do the same. So just back off of her and she will eventually put herself out there on her own , once she realizes you aren’t wasting your time on her like you were

[Asker]

I don’t even think she wants to date though. I think she’s happy with just being alone. It’s so sad though, I think she’s missing out

[Finchie40]

Yea I felt the same way about my brother as well because he is a great guy , he just had his heart broken by a selfish bitch that only cared about herself, I always encouraged him to move on from her selfish ass and find himself a girl that isn’t selfish , he kept telling me he is fine and feels better alone. so your girlfriend is probably the same way he is and sadly there is nothing you can do about it , it has to come down to her decision

[Asker]

True, I mean she lives a full life. As shy as she is, she does have good friends, she travels a lot and has hobbies and a career that she loves so I guess it’s possible to be happy single. I just never could imagine missing out on love so it’s not like she has an empty life. I know she’s happy, it’s just incomprehensible for me to understand why she’s okay with it, and in all fairness I’m the same way with my guy friends who are happier single too.

[Finchie40]

Has she ever been in a relationship before? If so , Did it end bad? Usually after someone has their heart broken , it’s sometimes hard for that person to trust again and they realize they are better off alone and no longer want the drama of a relationship , it’s easier for them to do without.

[Asker]

She’s had a few, all ended because of her not having sex. That’s just the thing, she is as slow as molasses when it comes to having sex. She takes her time with it and get’s dumped when the guys get impatient.

[Finchie40]

Yea sadly her chances of finding a guy that has patience and is willing to wait to have sex , is sadly going to be harder for her to find. I’m not saying she can’t find it , but she pretty much has slim pickings if that’s the route she wants to go. Most guys’ want sex , and if he isn’t receiving sex from a girl , he will more than likely find someone else that doesn’t withhold sex from him. Me personally couldn’t date a girl like that lol

[Asker]

Most guys don’t. One of my friends compared dating her to owning a Porsche without an engine: very pretty to look at but pointless to have if nothing ignites. It sucks so because she has so much to offer otherwise and I have men asking me left and right to be fixed up with her (my bf’s friends mostly), so it’s not like she can’t attract a man, it’s that she won’t fuck them. I’m starting to think she might be asexual tbh.

[Finchie40]

That’s a possibility , I have met some asexual girls’ before and all they like is the emotional connection but no physical connection

[Anonymous]

As much as you may think that’s all it is, I’m sure there’s a lot more behind the curtains. First of all is she really pretty. I don’t mean pretty by women’s standards. Women like to say their friends re pretty when from a man’s point of view they really aren’t. But that’s cause women don’t like to hurt their friends feelings. Now if she’s pretty as you say she is she should have had no problem meeting a man. Men would flow to her like water. But what will keep her single at that age is she probably has issues you don’t know about. Seeing as how she’s much older, almost as old as me, that means she should have met men who aren’t really like the men of today. Maybe I’m wrong but I think she has more issues than you think. That’s why she’s single. Your friend asked why she’s single at that age cause red flags were flying in his head. It’s different if a girl was married for 10 years or something, had a kid. That is understandable because maybe the man cheated or divorced her. Sure she could have done the same, but it shows a little history of what she’s like as a partner. But doesn’t sound like she’s ever actually had a real relationship. Don’t think she’s had kids or ever married. Those things singnal red flags in men.

[Asker]

No, I have men friends who meet her asking me to fix her up with them. She refuses and insists that she doesn’t want to date and doesn’t want to be fixed up. The only reason she’s even on the apps to begin with is because I’ve been on her ass to get out there dating.

She says she’s been hurt badly, the last guy she dated two timed her and cheated on her with his ex, and then ended up marrying the ex. She knows not all men are like that guy, but to ensure she doesn’t end up meeting another guy like him she just won’t date period now, no matter how much I keep trying to tell her not all
Men are like him.

I personally think the fact that she doesn’t have sex is what also caused her to be unlucky in relationships as well, but she’s not budging that either. She says she has found peace in being single and doesn’t want to disrupt that. She can find peace with a decent man too IF she steps outside of her shell, which she doesn’t want to do.

[Opinion Owner]

So then let her be. Maybe the men she wants actually don’t want her. Who knows. But it does sound like there a number of things there that are keeping her where she’s at. The men who ask about her are probably not the men she wants. But yes sounds like a lot of problems there for sure.

[Asker]

She does struggle with social anxiety disorder so I think that may be an issue too

[Opinion Owner]

I’m sure it is. Those are things she’s going to need to learn how to get over if she wants to meet someone. Otherwise chances are she will be alone the rest of her life. If she’s content w that then I think you should just let her be.

[Asker]

The other problem is she’s set in her ways. If she’s interested in a man, she will never ask him out, she instead waits for him to make the move and do the asking out. If he does call her, she won’t answer, even if she’s not busy. She’ll let it go to voicemail and call him back. When a man calls me, I’ll stop whatever I’m doing to answer him and talk to him. If a man asks her out, she’ll make him wait an entire week to take her out and insist if he’s really interested, he’ll wait (men lose interest at that point in my experience). I’ve tried telling her that the old fashioned way doesn’t work anymore. It’s 2025 now, women should be the ones doing the asking out, planning and paying for dates, proposing marriage, etc. I never waited for a man to ask me out, I always did the asking out. I was still single at 40 also, but I spent my entire adult life actively and aggressively chasing love and romance. I got hurt and all it did was give me more fuel to keep trying. Granted I didn’t chase my current guy, he chased me. I was only interested in a one night stand with him, but he ended up winning me over. She used that as an example as to why women should never chase men, but I think the whole “let the men do the pursuing” mentality is just a bullshit excuse to stay in her shell. It never worked for her and at 40, she needs to be the pursuer, and she needs to make herself readily available when a man spontaneously asks her out.

[Opinion Owner]

Well it depends on what kind of relationship you want. Most women who do the chasing end up realizing they don’t like this man after all. That he’s not masculine. She’s always planning things, he might want 50/50 w her, maybe a little feminine. I get what your friend is saying but the way she’s doing it, to men it looks like she’s playing games. So of course they’re not going to wait around. I do still think men should take care of a majority of things in a relationship, especially financially if he has the means to and is willing to. I’ve been w my girl for 16 years. She has t worked since our 3rd year together. She takes care of the house, kids, the dogs, etc. But that’s what we both wanted. Sometimes when women pursue men it’s seen as more masculine so men may be turned off by that. Sure they may date her for a while, sleep w her but after a while there’s a good chance they will dump her. I think your friend just has too many issues that she’s stuck in her ways. They’re never going to change so most likely she will be alone. And at that age it’s even harder for women to meet a man who will devote his life to her.

[Asker]

That’s I’m saying. She’s just always been very shy. I’m not shy at all so to me it’s just weird that she wants to keep her amazing, colorful personality to herself rather than share it with the world.

It’s definitely not impossible to find love at 40 (or any age), it’s not even hard as long as you’re willing to bend a little and change your dating habits. I was the aggressive one and yes, men did see me as being masculine because of that. I was also the woman who got a phone call from a man and ALWAYS answered, if he wanted to see me that night I would see him. If I had plans, I’d cancel them, so yeah I guess was the beck and call girl, and yes I got dumped so I get it. Then in walks current guy who actually pursues me and asks me out and it was scary, because it was out of my comfort zone (I did tell him upfront though if we get serious and he doesn’t propose in a year we’re done. Our one year is in May and he’s already told me he’s got a ring in mind). So I stepped out of my comfort zone and found the love of my life. She likes to point that out every time I nag her to pursue a man, but I always turn it back on her and tell her “I found love because I stepped out of my ways. If you would step out of yours and ask a man out, you probably would too”.

[Asker]

And also, at 40 I think her only option is being the pursuer.

[Opinion Owner]

No one said it was impossible. It’s just harder, especially for women. She raises a lot of red flags in men that’s for sure. She would if w me if I met her. But if she’s ok w that that’s her choice. I don’t think I’d push her. It I’m glad you met someone. The it’s good for you.

[Asker]

I think I figured out what her problem is. It’s the fact that she won’t have sex (which I’m almost positive is due to anxiety and PTSD). I know a few of the guys she dated years ago and all of them said the fact she wouldn’t fuck caused the break up. And the last guy too also said she was too prudish for him and he knew the ex knew how to satisfy him, hence he dumped her and went back to the ex. Yeah there you have it. She doesn’t really seem to want a boyfriend and the guys are figuring this out and dropping her. Unfortunately I think she is going to be single for life, not understanding why she’s happy with that but it’s her life I guess.

[Opinion Owner]

I’m not sure if she’s “happy,” she’s just content w it. She more than likely knows she’s the one who’s sabotaging herself. She might even be doing it on purpose cause to scared of getting close to someone.

[shortster]

She doesn't need to have sex with guys she is dating. Though setting her up is probably best.

[jahaims]

You're trashy and she has self respect.