Dating for Dummies

A few people who I know and love (hi, Greis, Issa, and Jenna, among others!) have mentioned recently that they don’t know how to date. And I have had so much experience with it, that I figured, what the hell. I’ll write a little how-to guide for y’all.

(I’m a giver. You’re welcome.)



This is where the vast majority of my dating experience comes from, so hopefully I can help out with some useful information here.

Which site to use?
Personal preference, that’s really up to you. I met Dave on, but I’m currently on OkCupid. I’ve heard good things about eHarmony and PlentyOfFish, too. One thing to keep in mind is that the market on each site may be vastly different based on where you live. So check them out, see which one feels the most comfortable to you (and which one gets the kind of search results – excuse me, I mean guys – that you like), and go from there.

Your Dating Profile
A few points to note here:
1. Be honest. Don’t pull a bait-and-switch on anybody. Like, I’m never going to put on my dating profile that I “love the outdoors” and lure some poor schmuck in by thinking that I’ll go camping with him, because you know what? No. It’ll never happen. And I’m not going to talk about sports that I like, because I don’t like any of them. Sorry, dudes. What you see is what you get.

2. Be funny. This is SO HARD on a dating profile, but seriously, just work in some mild humor where you can. It goes a long way. (If you want to know my OkCupid username so you can go look up my profile and copy some of my stuff, let me know and I’ll email it to you. I’m just not posting it here, because… uh. No. Separation of church and state or whatever.)

3. Post a current picture of yourself. I know, it’s shallow. We should be judged on the content of our characters and not by our appearances, right? Well, sort of. Look, I’ll admit it, I’ve turned down some guys that look perfectly nice on paper because I was just flat-out not attracted to them. It happens. One guy had a 97% compatibility match with me (97%!!), but he also had a long twirly handlebar mustache. And I’m sorry, I know it’s shallow, and you might be otherwise perfect for me, but I cannot possibly think about making out with you if you happen to look like the villain in an old black and white movie who ties the damsel to the train tracks. Just, no. Your face killed my lady boner. Sorry, dude.

Also? Something I heard from one of the guys I went out with – don’t do the “MySpace Angle” in your profile picture, where you take the picture from 3 feet above your head to make you look thinner than you are. He wasn’t an asshole about that, btw – he liked me and lord knows I’ve got a little extra chunk on me – his point was that it’s just a misrepresentation. It comes back to that whole “be honest” thing I said in point #1.

Using the Dating Site
This is kind of a weird double standard, but it’s true. If you’re a female? You kinda don’t need to do much at this point. Once your profile is posted, you will most likely be contacted by a lot of guys.

But, if you want to search and find some guys that you want to contact yourself, hey! Awesome! Go for it! I did it once or twice myself. Sure, some guys might be put off by forward women who initiate the first contact, but those guys are clearly insecure and have tiny penises, so let’s roll our eyes and feel sorry for them and move on.

KEEP IN MIND! You are going to have to do a LOT of weeding. As we all know, the Internet is full of sketchy people and creepers, and dating sites are no different.
* I can almost guarantee you will get approached by at least a couple of guys who are very plainly just looking for a one-night stand. You don’t owe them a polite reply. Ignore, delete, move on.
* You will also most likely be contacted by many guys who are married and “looking for a discreet encounter.” (This happens to me surprisingly frequently.) Which, eww, right? Those guys usually get a curt reply from me that says, “I don’t f**k married men. Bye.”
* You may also get emails from guys who are in “open relationships,” and don’t even get me started on that topic, because hey, consenting adults and as long as everyone uses condoms and whatever, but bottom line? Not for me, thanks anyway, move along.



Ok, so let’s say you do your online dating profile and you end up chatting with a guy who “gives good email” (heh) and seems compatible with you. Here are some ground rules for the first date. Some are safety oriented, some are for your own sanity.

1. Yes, it’s ok to give the guy your cell number so you can text each other. This is pretty common practice nowadays.

2. Have a go-to “first date” outfit. It’ll save you time and worrying if you go out with more than one person. (Plus, the whole, “Wait, did I wear this when I went out with him last time?” thing.) Mine is a particular pair of jeans (which I call my “good butt” jeans) and a cute top with a pair of wedge sandals. (Gonna have to rethink those shoes for winter. Hmmm.)

3. For the first date, meet in a well-lit public place. He doesn’t need to know where you live, and you don’t need to get in a car with a virtual stranger.

4. Make sure someone knows where you are. If you’re nervous that it’s going to be awful, have a friend text you at a certain time (about 20 minutes into the date) in case you need to make a quick exit. If you’re having fun, you can ignore the text. (Honestly, I never do this anymore. I figure I can suck it up and talk to pretty much anyone for an hour or so and it won’t kill me.)

5. The best possible plan for a first date is to meet for coffee (during the day) or a drink (at night), but no meals. If you’re having a meal together, you’ve committed to a big chunk of time. For a coffee/drink date, you can easily drag it out if you’re having a good time, or you can cut it short if you’re not. It makes it easier and less awkward for both parties.

Side note: Do not go see a movie on the first date, or even the first few dates, really. The idea is to get to know each other. You don’t get to know someone by sitting next to them in the dark and not speaking.

6. Remember the weeding I mentioned earlier? Yeah. You’re still gonna have to keep doing that. Some guys you might go out with and you don’t feel it. Or you might like them a lot, but they don’t feel it for you. Rejection sucks in either direction, but it happens. You’re probably going to go on a lot of first dates that don’t lead to second dates. It’s just how it works.



1. This is hard, but try to be a little thick-skinned about it if someone blows you off. Likewise, you need to have a (preferably polite) blow-off message to send to someone who may be interested in you, but who you aren’t interested in yourself. This is rough. Mine is basically this:

“Thanks, I had a really nice time, but I just didn’t feel that ‘spark’ or whatever, and I know myself well enough to know that if it doesn’t happen on the first date, it mostly likely never will happen. I’m really sorry, and I wish you the best of luck in finding your match. Take care!”

Something like that, more or less.

2. On the other hand, if he digs you and wants to see you again, and you dig him and want to see him again… well. From here, I’m guessing you can probably figure it all out for yourself.


Ok, that’s basically it. If you have questions, let me know in the comments and I’ll try to answer them as best I can. (Oooh, maybe this will be a multi-part series! Fun!)

Happy hunting, ladies! XOXO

10 thoughts on “Dating for Dummies

  1. You have terrified me. Truly. open relationships? Men who say they are married? Whoa. I have a shit load to learn. However, this is actually helpful. 🙂

    Thank you for doing this. Also for cracking my ass up.

    I know I have more questions…but I’ll save them for a later date. You know when I go beyond the marinating the idea in my head part that I’m in right now.
    Issa´s last blog post ..Three years and maybe now I’m ready to move forward. Maybe.My Profile

  2. It’s not that I don’t know “HOW” to date, I just truly suck at it. And the weeding through the crazy people, it’s the same reason I don’t shop at Marshalls/TJ Maxx I don’t like to dig through things to find what I want.


    This is awesome though!!
    AmazingGreis´s last blog post ..Thirty Four…My Profile

  3. Love this! I am the token single lady of my group of friends. ALL of them are pushing me to take the plunge because they all had such great success with it. I am petrified. I know that Prince Charming is not just going to drop into my lap, that it will require me to put some effort and work into it. *sigh* All the signs are pointing to JUST DO IT. This post is one of them. Thanks Cindy, unbeknownst to you, you have been an inspiration through my divorce and single parenting saga. It’s time for me to put up or shut up. 🙂

  4. Good stuff, Cindy. This will help many who need a step-by-step overview when stepping back into the scene!

    Well most of y’all know I won’t do the dating site thing. Yep! Chicken. It’ll happen organically or it won’t. BUT! I have lurked before. And it’s … interesting?

    One thing I’ll add (and I hope y’all do this)… if you don’t have a Gmail acct, get one. Then sign up for a Google Voice phone #. It’s free and you can pick one in any area code. You can link that to most any cell and still text normally without giving out your actual cell. I’ve had my cell # for almost 15yrs and have zero desire to change it because a resident of Crazytown has my digits. So look into that when entering the dating world.

    I wish everyone fun on your chosen path to finding that special someone.

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