Dating Tips & QA

Dating Q&A

Sex on the First Date?

“My mom thinks me dating means I’m going to be sleeping around a ton. It seems  lots of people do have sex on the first date. Is this okay or should I stick to date three? I’m in my twenties.” Meghan from Calgary, Alberta


We need to stop thinking that sex on the first date is an indication of loose morals. Meghan, darling, if you want to have sex with a guy on the first date, you go ahead and do just that. If you’re feeling it, and he is, and the timing is right and everything is aligned, why deny yourself one of the more wonderful experiences in life? Life can be shitty as it is, so grab what awesome it sends your way.

What you do on a first date is nobody’s business. We all have are own comfort levels, so choose yours and go with it. If sex on a  first date doesn’t feel right after all, then don’t, and let your date know if it goes that way. If he bails rather than waits, then you have a clear idea as to what he wanted and where he’s at mentally regarding relationships and moving forward in any capacity. He wants sex only probably.

Sex on a first date does not mean you are “loose.”

Sex on a first date can help you both figure out if you are compatible sexually. If you can’t work it in the bedroom, then why bother moving forward? My two cents. Unless you are fine with a sexless or meh sex life. I’m not.

Sex is fun and feels good, so if a moment and opportunity shows up I say go for it and enjoy it. Unless you’re a teenager. I don’t recommend this attitude for anyone under 18.  Just be safe and practice safe sex. Other than that, fall into bed and enjoy the moment and the beauty of your bodies coming together, if even for a short, sweet time.

Dating FYI, Matchmakers

Matchmakers: Yes or no?

Matchmaker, Matchmaker…

Matchmaking is another way to meet men if online dating isn’t your thing or you’ve tired of it. It is definitely a more civilized way of meeting a potential match for a number of reasons:

  • Your matchmaker takes time to get to know you through various methods (in-person meeting, questionnaires) and then hand selects a person for you.
  • The matchmaker will have met both you and a potential match, so some level of screening has taken place.
  • It saves you the time and hassle of weeding through hundreds of men online, and having many pointless conversations just to filter down to the two or three you might want to meet.

I’ve researched local matchmakers and contacted three last November. I went with local boutique type matchmakers and not the huge ones across Canada. I’ve heard from reliable sources that the large matchmaking services (not all) often charge thousands upon thousands of dollars and sometimes get you no picks or just pick any old person for you just to say they got you matches. So I picked local women who had tiny firms. I picked:

Single in the City

I paid the $125.00 initial consultation fee and waited for Laura to call me to set up an initial meeting. The $125 is a one-time fee and then you pay $50 for every date she sets you up on. Seems reasonable. That $125 includes a $50 credit towards any event she throws.

It took her four days to get back to me. She seems a little stiff on the phone and wouldn’t  meet anywhere but downtown or in Oakville. All three matchmakers actually only would meet downtown. So if you don’t live in Toronto you are SOL where matchmakers are concerned, unless you travel to them, and live within the GTA (mostly). This is an open market as far as matchmakers go. Maybe I’ll start up my own boutique lol

So we met and Laura was the sweetest, friendliest woman. Warm and intelligent, and easy to talk to. We chatted for two hours, and most of that time had nothing to do with men or matchmaking. We just hit it off. She went through my questionnaire, took some pics, and then said if she found anyone in her database she would let me know.

It has been six months! No matches. Well, one, but that 55-year-old declined meeting me. I wasn’t exactly hot-shit keen on meeting him because he’s as old as Moses as far as I’m concerned, but I was willing to try. I guess 42 isn’t young enough for him. Surprises me not.

Shanny in the City

I actually interviewed Shanny for my book months before I reached out to her about matchmaking services. She doesn’t recall that I did. I am predicting her fees will be high, like four to five to ten thousand dollars, so I am actually hesitant with going through with this because how awkward to say I can’t afford you even though I *know* she’d find me a man no problem. I just sense that about her.

The first meeting is $125 as well, but I had to cancel. One, she scared me, and two,  for the money she will charge, I don’t think I am ready. And … I don’t currently have the money she will charge, but paying it might be in my best interest to find a professional, attractive man with a good job and money. I will use her if all else fails. My last ditch effort as it were.

Friend of a Friend Matchmaking

This one I thought I might not hear back from because they even say on the application page that if you don’t get selected you won’t hear back. It’s based on your location (HAVE to be in Toronto) and what you write. I begged for them to pick me and said it’d be no problem getting into the city. But I did get in. Yay!

I got a code to enter a website where I paid my $427.00 (I know, kinda pricey), but if you consider how much online dating sites cost (the paid ones like Match, eHarmony, Zoosk, and even Plenty of Fish if you upgrade for $20/month) this isn’t that extravagant at all for a year. I paid and then got to download a terms and agreements page and then the 30+ questionnaire they needed me to fill in so they can match me with the love of my life.

(I am skeptical, gotta admit, but best to have all hands on deck with this one, especially since I don’t have family here to hook me up with someone, many friends here to hook me up with someone, and work from home. And I go to Pilates which has one man in the whole group. The gym you say? Please. I’m sweaty and gross when I go. And I wear sweats and old T-shirts a lot of the time so nobody is going to check me out. And who has ever gotten a date from the gym? Yes, Miranda on Sex in the City did. But not in my world that doesn’t happen…not yet anyway.)

I met my matchmaker January 3 in a coffee shop and they asked me a whole bunch of questions. It lasted 45 minutes and I was on my way. So matchmaker, matchmaker…make me a match. But it hasn’t happened yet! Not one hit from them. Am I that unmatchable? lol

Matchmaking does work, I’ve seen it work. It just hasn’t worked for me.

Boutique agencies are the way to go in my opinion, because they often are more affordable, and more legitimate. Read the terms and do your homework. If you live in Toronto, any of those three firms (or all!) will be great for you. Wonderful women who just want to help you find the perfect match.



Dating Q&A

How to handle the “I’m submissive” question

“I started talking with this guy online and he says he likes to be submissive and have the woman take control. I’m not totally out the door because of that, but I want to know what exactly he means. Like, how far does he take this? Can I ask him to explain further?”  Tina in Oakville, Ontario


Tina, you can definitely ask this guy to clarify what he means, because it could impact if you want to continue talking to him and even meeting him. Why waste valuable time going any further, yours and his, if his answer is something you aren’t comfortable with or into?

BDSM is a thing for lots of people, and it can be fun and exciting, but you have to be comfortable with it. When someone says they are submissive I think you are definitely okay asking for clarification, because who knows how far he takes this into every day life. You should know. 

I had a similar situation happen to me. Guy said he was submissive and wanted a woman who took control. I thought about this and the next day asked him what he meant. Did he mean in every area of his life? Could he make decisions or did he prefer the woman make them all? Would he make any moves and initiate at all?

He answered the questions and clarified a bit, but I could tell he had gone cold. I don’t know why because open communication is important and he was the one who dropped the “I’m submissive” thing in the first place, in the first thirty minutes of our talking.

He then messaged me and said he may not be the guy for me. I said okay, he was judging a bit fast maybe, but thanks anyway and nice talking. His reply? “Go fuck yourself.”

Huh? He’s 28 and his age showed right there that minute. Dodged an asshole bullet I think. 

Anyway, if someone offers this information up, I think you have every right to ask questions if you need to, and he can tell you to fuck off or be a proper human and engage in decent, open communication with you, because even a purely sexual relationship needs good communication between both parties.


Dating Dos and Don'ts

I Dated Hard and I Did It for Research

When my marriage ended almost two years ago, I went online right away for a number of reasons. I wanted to distract myself from the crumbling foundation of my life around me and wanted to meet men to see what was going on 11 years later.

I went on first and paid my 80 or whatever dollars, loaded a picture, and a created a profile write-up. It felt empowering to be on there. I chatted with a few guys, and then decided to try another site and joined OkCupid. Now I was chatting with more guys and discovering a world I had never known existed, and was learning terms I’d never heard of before.

And behaviours. Whoa. Talk about men behaving badly!

Two months in, in January 2016, I decided to take it seriously, for actual dating now perhaps, to meet men rather than just remaining faceless and chatting only. A few weeks into that, I wrote an article about the breakdown of my marriage and my takeaways from online dating so far, though that crazy journey hadn’t even really begun.

A friend read the article and suggested I turn it into a book. So I did. I planned on doing a year in the life memoir of my online dating experiences and would learn everything I could, and experience as much as I could, so I could report back to other women via my book about what was out there and how it all goes down. And we would see if love had found me after a year.

That book won’t make the light of day. It’s too damn personal. What I did, though, was turn it into a quick and dirty guide to online dating based on my experiences and takeaway so that other women heading into the pond have an idea as to what might hit them while swimming in shark-infested waters.

I’m working on self-publishing that book and will post a buy link on this site when it is ready. Traditional publishing simply takes too damn long.

But why am I qualified? Well, I chatted with hundreds of men over the course of a year and a bit, went on many dates, and so I feel have a really good handle on men and what dating online is like, because… I dated hard and I did it for research lol. 🙂

Dating Tips, Uncategorized

First Date Ideas

Dating should be fun.

First dates, and even second and third dates, can be stressful, awkward, and downright nerve-wracking. Make sure you both agree on the activity you do so you both feel comfortable…and enjoy it!

Here are some date ideas, whether it is the first or third:

  • Coffee/tea/smoothies. Standard first meeting activity. Not really a date per se, more of a way to screen the person you might consider dating.
  • Museum.
  • Dining in the dark. Risky, but exciting at the same time. I have yet to find someone willing to do this with me.
  • Park walk. Casual, not so in-your-face intense, and allows for easy conversation because you can pick topics based on what you see etc. You can learn a lot about someone based on a walk.
  • Bumming around the downtown core. Fun because you get to do a variety of things and conversation will likely never be at a complete standstill. Unless you’re both truly boring lol.
  • Bowling.
  • Roller skating.
  • Aquarium.
  • A local fair.
  • Amusement park.
  • Going for ice cream/gelato.
  • Some kind of sports activity.
Dating Dos and Don'ts

Are You Ready to Start Dating Again?

After separation and divorce, you need to be honest with yourself once you decide to get back out there. You should ask yourself the following questions:

  • Are you ready to start dating?
  • What do you want? Your options are Friends With Benefits (FWB), relationship, to date a few men, hang outs, and hook ups.
  • What does he want?
  • What did I do that contributed to the breakdown of my divorce/separation?
  • Are you over your ex?

The only one who can determine if you’re ready to start dating again is you. Some people say you need a month for every year together.

Others spit out two years as the magical number. And then there’s everything in between and sideways of that.

You will know when you’re ready to be with another person when you want to be intimate, emotionally and physically.

If you still have feelings for your ex, you aren’t ready. If you still cry over the break-up, you aren’t ready.

If you never think about them and feel excited at the prospect of meeting new people, then you are as good as ready. You can be scared and uncertain and doubtful of your success, yes, but you are otherwise ready.

Dating helps you figure out what you will and won’t tolerate, what you do and don’t need.

Date a lot, meet a ton of men, sample the pool, see what’s out there until you find what fits for you and makes you feel good.

Dating is exhausting, though, physically (all that prep work!), mentally (trying not to think “not another date with some guy I probably won’t like”), and emotionally (you think it went well but … you never hear from him again. Awww, that kinda hurts, dude).

Men who are already built need only apply.

And that seems to be a tall order these days.

I am not a charity. Say this to yourself too.

We need to make decisions that benefit us going forward.

We need a man who is already built.

Take some time to figure out if you’re ready to really start dating. Maybe you won’t know until you try for a bit. You will figure it out pretty fast once with other men if this is for you right now. And if not, take more time and try again in a few months.

Dating FYI

It’s Confusing Out There!

Dating today is complicated, like really complicated. Even down to the phrases and terms we use.

I didn’t know any of this when I started, so I’ve been bumbling my way around and have learned everything the hard way.

One of these crazy terms is Netflix and Chill. Maybe you know what it means, but I certainly didn’t. In the first few months online, men would use this term with me and I literally believed it to mean watching Netflix on a couch and chilling, hanging out. Aww. Sounds really sweet and cozy. One would presume it means, “Hey, let’s watch some Netflix and chill and cuddle and get to know each other.”

This is not the case. Its real meaning is, “Hey, let’s have sex while Netflix flickers in the background.”

AKA booty call.

Beware the Netflix and Chill. I’d be so pissed to show up at some guy’s house and end up not watching Netflix. If this is what you want, now you know what to ask for.

Another term to know is ghosting.

Ah, ghosting. It is awful to experience and men love to do this. It applies equally to those you have only messaged with, whether it be three hours, days, or weeks, as it does to those men you have met and even dated a few times.

Ghosting is when the guy simply disappears, vaporizes, is no longer around. Vanished, like a ghost. You might literally be in the middle of having a great conversation with a guy and then there’s no reply for a day, then three, then a week…girl, he’s ghosted on you if this happens.

For whatever reason only known to him, he has determined that this thing between you two isn’t working out. Why? Lots of possible reasons:

  • He thinks you will move too fast.
  • He only ever wanted a temporary texting buddy.
  • He realizes you aren’t going to give him what he wants.
  • He met someone else.
  • He got bored.
  • He never had any intention of meeting you.

You will never know, and, frankly, he doesn’t owe you an explanation. It does seem rude and cold, but what are we supposed to do otherwise with someone we have only known for a short time? It makes dating and people disposable and that’s the part I hate.

This is dating today. You meet a lot of new people and most of them end up ghosting and you never hear from them again. Sometimes they reappear and you can decide for yourself if you want to re-engage or just ignore them. But whatever you do, do not ask the ghoster why he ghosted. Do not send four or even one message asking if you did something wrong.

Let it go.

Your “closure” comes in his non-response. Move on to someone else who will see your worth and want to pursue you. That’s it. Don’t take it personally, though it feels very personal. It isn’t. This is how it is done today, like it or not.

I didn’t make the rules. I am simply sharing them with you.