Younger cousin getting married

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So I really am a sociopath. I knew it all along. Now I just have to go find some nuns to brutally murder and a place to store their heads in.

She most likely will. But if I am not invited, it doesn’t do me any good. I’ve actually been told I am “too old” to be around women ten years younger than me even though I sometimes see 40 years old or even elderly men with young women. I’ve even seen a young girl having sex with a guy in his late 30’s or 40’s on a “fling site” I tried out of desperation.

I’ve had elderly women flirt on me. These aren’t well aged women like Cassandra Peterson (Elvira) but “little old granny” types so it’s embarrassing.

It doesn't matter what you've been told. If you meet a young woman you fancy, chat with her and ask her out. If she says no, she says no, but it's important to try. That's the only way to build your confidence. She doesn't need to flirt with you. You might not know her flirting signals and she might not give any if she is reserved.

Go to the wedding if at all possible, but go to enjoy yourself more so than to find a girlfriend.

It's important to keep involved in social activities as much as you can and to find pleasure in your day to day activities.

How have these "grannies" flirted with you?

I guess this could happen----but I feel that, most of the time, these grannies just want to treat you like a son. This involves "mothering" you. To people who don't understand "mothering," it could seem like flirting.

Maybe the "granny" doesn't have a son, so she "mothers" you instead. Or even if they do have kids.

Perhaps, the "granny" just likes to "mother" people.

It's not sexual in the vast majority of instances.

You're not too old to be around women in their 20's. If anybody says that, they're out of their minds.

Well, my therapist told me to not seek out relationships because it apparently makes me look desperate but I always feel like I am missing out. I just don’t know if it’s ok to approach women at, say, at a coffeehouse. Is it even ok to offer to buy them a cup of coffee?

Just talk to these women, Marknis.

There's, of course, no guarantee that anything will result from these conversations.

But it's good practice, nevertheless.

Don't talk about anything serious. Talk about the weather or whatever. Or whatever they feel like talking about.

Who knows? Maybe these women are into "alternative music" like you're into "alternative music."

I agree with kortie. You can talk to whomever you want, just try not to have preconceived expectations of what will happen. Keep it casual with a desire of getting to know people. You don't need to have a game plan every time you say hello to someone. To be honest though, I wouldn't recommend offering to buy someone coffee in a coffee house unless you've already been chatting / sitting with them for quite a while. Most people are in coffee houses with friends or else they're alone and working on a computer / reading. If a stranger randomly wanted to buy me something I would feel a little uncomfortable. Saying hello and "What kind of frappuccino do you get? I never know how to order here..." would be a better conversation starter.

I went out to a coffeehouse and the only girl I found attractive was not only on her laptop but had headphones on as well. I got stricken with anxiety about what I should do and left. My mind is saying I will never overcome my approach anxiety and I’ve fallen so far behind so I should just give up on love completely except that I don’t want to keep living.

I think it's great that you went to a coffee shop. Some people would be too nervous to go at all (me, for instance). Consider it one step forward because you tried. Don't take it a sign you need to give up. I hope you got a coffee and enjoyed the experience rather than rushing out when you felt anxious, but either way I understand. I hope you can keep trying new places and doing things that you enjoy every day.

I can tell you from experience that chatting with women who invariably show that they're not interested in you will not build your confidence. Quite the opposite.

I agree. I'm saying that he doesn't have to think of everyone as a potential date. General conversation with people at a wedding or social activity, and polite random conversation, will help him (I hope). I'm talking about conversations with women who aren't judging him as a potential date or deciding whether or not they're "interested". Talking in general, in a variety of settings, will help people to feel more comfortable when the right one comes along.

I disagree with the others. It's generally not a good idea to randomly approach people in a public place because you're attracted to them, unless you can read them and they seem like they'd be open to it, have open body language, etc, or maybe if you're somewhere where it's more socially acceptable to do something like that, like maybe a bar or a club. It's generally better if you have a group of friends with you too, for "social proofing". You also have to be prepared for the fact that you're more likely than not going to get rejected.

The problem with approaching people randomly like that is success is very much dependent on your physical appearance and social skills (since that's all the other person can gauge from you initially), so if you're lacking in one (or especially both) if those areas, it's not a good strategy.

In my late teens, I tried approaching probably about 10-20 women like this, and all I got from it was a knock to my self-esteem when it never worked out in my favour

Isabella wasn’t talking about approaching women blindly.

She was talking about Mark speaking with women who are sitting at the same table as him at the wedding.

Yeah, at a wedding or social event or something like that, I'd agree with you, or where he and the people he's talking to have mutual friends.

I don't think a coffee place is a good place for it though. Most people just want to enjoy their coffee or meals.

Exactly. I'm saying, talk to the people at the wedding. Talk to the cashier in the coffee shop. Talk to random people even if they are married. Actually, talking to married women would be great because he can "practise" having conversations, making small talk, getting to know people, and feeling comfortable chatting with women without having to wonder about dates. The more often this happens, the more prepared he will feel when he meets a potential partner.

TGI: I agree a coffee shop isn't a great idea, and I said that somewhere earlier. Most people who are alone have their face in a book or computer screen.