I Love Computers and Technology

Woo thanks a lot, I'll try and check that one out too! As for security yea, nothing is ever fully secure. It's always a game of 'cost of security, value of what is protected, cost of breaking the security '. If a nation state is after an individual they'll get them. What I look for is reducing the attack surface and upping the cost past my potential value so it is too expensive for individuals / creepers / profiler tools / and hackers to bother with. Also to stay out of general reach of common law enforcement (on principle) so the only groups who might break in would not consider me enough of a bother to follow up.

Skype is fine on encryption to some degree but it is not end to end (Skype the company can decrypt and then use it to sell your data/ profile, especially now that MS owns them and has that giant data gathering push shown in win 10) and there are a lot of tutorials available for creepers to catch the IP and find it who you are. I do use it (video is top of the line) but only with friends or people I know reasonably well. (If I wouldn't give someone my phone number I generally won't skype with them). And I avoid certain topics.

The tools I've liked (why I ended up with the one I did - and I'll totally check out the other one) don't track personal data (address books, phone numbers, etc), don't store stuff on their server (though some said they didn't and independent reviewers found out otherwise) so they can't become a vector to attacks, the encryption is between the end points only (company doesn't have a description key), and the communication doesn't reveal information to the other party about who you are (until you are comfortable sharing it).

It's a bit much for private individuals but I've had people go stalker-nuts, my gf has had stalkers, every girl I've known has had at least one guy/girl who was just... *shiver* so yea. And I've seen enough ad tools to know how damaging it could be if they get too much data (they can inadvertantly reveal it - like when that one company emailed the girl congratulations on her upcoming baby and she hadn't told her father yet - or just mind manipulating you into purchases, or selling your info and generating spam, or tracking your friends through you..)

Some I rejected over this ( http://venturebeat.com/2014/10/28/whisper-secret-and-snapchat-leaks-show-that-fake-privacy-is-almost-worse-than-no-privacy-at-all/ ). As for Telegram there were minor problems (eg. http://www.pcworld.com/article/2871412/how-much-trust-can-you-put-in-telegram-messenger.html ) but I think I just skipped it because of the big iPhone focus, didn't know how much with they'd put in on the Android side.

As for vendors, yea, exactly. There are just some I have to choose to trust (eg Google) and that generally appear reasonably good at respecting privacy (or at least not distributing it past their own local needs). There are some that obviously don't care like FB and MS/XBone, and there are some that might be good... but are small and you can't be sure they know what they're doing.

For Windows.. meh, yea, there is very little there surpisingly, unless the people are tech savvy and want to / know how to put in a bit of extra work. I'm still looking at that :/

Most of those people asking you for Kik are fakes (men pretending to be women, or women far different than their advertised profile), so factor that into the equation too....

I went through a similar exercise and I also reject the obvious choices like Kik, for security reasons. Why do you reject Skype? Is their messenger a point to point application that exposes IPs? Almost everyone I know who wants to chat uses Skype, and because of the pressure I get from women on this I want to understand that app better. To be honest, the kind of women who typically pressure me on this I have 95% proof are real and harmless, so the lack of privacy becomes less of an issue for me.

The application I found that looks very impressive is VIPole. That includes text messaging as well as voice and video chat, all secure. Their servers are in Great Britain however.

You are fooling yourself if you think any of this security protects you from a government. The fact that you are communicating through a server outside the US actually means you become a point of interest for the government, and they may have means to break your encryption. So I think that is not the right way to think about it. The right way to think about this problem is that you do not want messages in the clear for individuals who capture information somewhere in the middle. For example, I once chatted a lady and the administrator of the system read all our messages, got her phone number, and started making "whisper voice" calls to her, claiming to be me. That was a nightmare to unravel. A good encryption solution for email and text and voice chat would make such a privacy theft impossible for everyone except a government.

Maybe after you look at VIPole you could write a review comparing it against Threema?

You raise a really fantastic new point here, which is that Android and iPhone applications often want access to your phone and contact list. Few people realize that Facebook uses this to grab all of those phone numbers and cross reference them against its registered users. If it finds a match, it then suggests you to each other as "friends". This is such a monstrous violation of privacy for everyone. So you are smart - and right - to look carefully at what permissions a chat application asks for when it installs. Unfortunately, I use these applications on my desktop more than my phone, and Windows 8/10 do not have good privacy tools to help determine how nosy any application you install actually is. Ultimately I just look at the overall design regarding security, and at some point I make a decision to trust the vendor or not. My conversations are so benign I don't feel I need to go crazy on my vendor review.

I laughed when I saw some of the tools available to help secure private messaging tools:
https://ssd.eff.org/en/module/how-use-otr-windows

While this works if you have two motivated people, the problem is that one end of the conversation might be an unsophisticated user. Just motivating that unsophisticated user to follow the complex install and authentication procedures above would take a long time. I generally find when women do want to chat with me, they have almost zero patience in changing their unsecure computer habits. And - ironically - if you are a person who cares about security and privacy, you are immediately treated with suspicion.

It's very difficult to get all of the moving pieces to work.

Threema looks interesting, but why did you choose it over Telegram? Telegram has the additional benefit of having a web-based solution, so it is extremely cross platform:
https://telegram.org/

Have you seen the EFF review of secure messaging tools?
https://www.eff.org/node/82654