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(AMENDED) Online Dating: Preparing Yourself

Oct 23, 2013

Sunday, October 27, 2013 9:04 p.m.

Screw it, I'm reposting this. My mom said she thought it was "a cute post," and ladies everywhere loved it. Dudes, if you don't like it...uggghhhhh... [delete delete delete].

Okay, look, I've got two eligible, dating bachelors in DC who are going to co-write a blog post with me to expound on this topic. If you have any questions for them/us, leave in the comments below this week. But don't be nasty or I'll ignore you, got it? I'm trying to make this a productive experience here. Let's attempt to be civil.

Thanks, all, for reading and participating in the discussion. I hope we can all still be friends.


Now that I'm single again, I've been receiving a lot of reader requests for my expertise on the many facets of online dating. Personally, I think I'm an expert at staying single, but hey, I'm happy to share my insider knowledge.

Today we'll explore prepping yourself to jump into the wonderful world of online dating. It's scary, hairy and very...what rhymes with hug me?... The point is, don't take it too seriously.

1. Google "online dating" and click the Images tab. Here are two of my faves.

Why would you ever do ET fingers with a guy you met over the Internet? 
Or hold hands like this? 
2. Don't go into it thinking you're going to find your husband. 

Listen, I know how you feel. My eggs are starting to go bad too. But we're all going to get married and will have babies if we really want to. You can't think about that right now. Chances are, you aren't going to find him online. Yes, I know your neighbor's cousin met her fiancee online and things are going great and you told your neighbor her cousin's ring is big when you really think it's merely adequate. SHUT IT DOWN. You are only doing this for fun, remember? Besides, you and I both know when you end up on a date with a guy who is clearly only interested in finding a wife, your interest level plummets. Think about that.

3. You may still be climbing the career ladder, but you are CEO of yourself. You got that? C-E-O. You're about to e-meet some guys who seem too good to be true (they are)...

...and some that seem icky but you're trying to be open-minded so you talk to them anyway.

Stop feeling bad (why do we waste so much time on feeling bad?) and take charge of yoself. Talking to strangers is just how it's gonna be, but you've still got your intuition, so use it. Don't feel like you have to talk to everyone who talks to you, but do be aware that if you are too selective in responding, you'll affect the algorithms that match you with guys in the first place. 

4. You're about to get rejected a lot. Deal with it. 

And don't take it personally. The truth is, as a girl, you're getting way more messages, winks, pokes, likes, and whatever they come up with next, than guys. And generally in life, guys get rejected way more than girls do. Think about this: By the age of 30, you've been rejected, what, a couple of times a year since you turned 15? So let's say 30 times. Guys get rejected every week. That's 780 times. (Please note: I conducted no scientific research, I'm just estimating.) Again, don't feel bad for them, but also don't make a big deal about it when it happens to you. There are plenty of other idiot guys to get attention from. 

We don't because we're hopeful and don't want to skew the algorithms, hurting our chances at finding that perfect match. But a lot of other people do. It's no big deal unless he's a serial killer. I've never encountered one of those that I'm aware of, so don't worry about it. If you do worry, I refer you to No. 3. And if you find yourself on a date with the too-good-to-be-true guy who clearly lied about his height, just enjoy the free dinner and ignore him later. 

6. Wait, I get free dinner? 

Yes. Don't pay. And don't settle for just drinks. Order food and don't reach for your purse when the bill comes. You don't owe him anything. If you start to feel bad, as we girls tend to do, remember that he asked you out, so you've already upheld your end of the deal.


WOW this point generated a lot of discussion. Here, I'm embedding this one tweet for the sake of argument (if you want to be thoroughly entertained, I recommend you go read the entire thread):
So, okay, fine, all guys want you to offer to pay. But guys, please know that we feel UGH about this.

It's not about getting free stuff. Most girls can get free stuff without taking the time to go on a date. It's not that hard, just show some cleavage and giggle. It's more like the consolation for going out on bad blind date after bad blind date. Growing up in the South, but I imagine elsewhere as well, I was taught to expect the guy to do the asking, open the doors, take you to dinner and pay the bill. We were the prize to be won. Well, news flash parents, 99% of the time it's not like that. So we lower our expectations and, in desperate moments, our standards.

However, the 1% is out there. I've dated him.

Here's the thing, fellas: If you treat us like what I'm describing, later down the road we are going to treat you like a king.

I'm sorry if I or any girl has made any of you feel like we're freeloaders. We just want to feel pretty.

The comment from Anonymous made me feel bad (ARGH I'm being such a girl) and that is the reason why I decided to amend this point.

For the record, because I have to state this just about every other post, most of my dates aren't terrible. Only the bad ones end up on my blog. And even then, only the bad ones with guys I don't suspect will ever read my blog end up on here.

And by the way, I still offer to pay the majority of the time. But when I'm out with a really classy guy, I don't because, at least to me, it feels like it drags down the classiness of the evening.

Now, when it comes to No. 7? Screw that. Y'all are on your own. 

7. But what if I asked him out? 

You didn't. Try, I dare you. You will get a 0% response rate. I don't care how modern you feel dating online...guys will never evolve from wanting to chase us. Let them. I know that one guy who keeps looking at your profile is your No. 1 pick and you can't figure out why he keeps looking but won't ask you out. It's because he's dating other girls he thinks are better than you. Neither you nor I want to believe that the guy we like thinks some other girl is better than us, but let's face it, you put that guy in your No. 1 spot which means you think he's better than all those other guys who are actually trying to talk to you. Enjoy the fact that No. 1 is hung up on your profile and move on.

8. Back up...what are these algorithms you keep talking about? It's a fancy term for, the guys who designed all these online sites are aware that girls are picky so they set up these technical thingies to keep you from getting attention unless you're paying it forward. 

The product of 15 years of rejection. I give you permission to feel bad in this case.

So just because your No. 1 is ignoring you, don't ignore all the others because you feel like somehow this is payback to No. 1 (who probably uploaded an old Abercrombie ad as his profile pic, by the way). Give them a chance. Don't go out with them if you don't want to. But give them a chance. 

9. You're going to see some gross stuff. 


I mean penises, of course. The first one will shock you and you'll feel violated and tainted and scarred for life, but after that just report the guy and pat yourself on the back for saving your fellow lady online daters from seeing that particular unsolicited penis.  

10. Married guys, guys who can't speak English, guys with weird fetishes, guys who know you're way out of their league, and guys who are just looking to get laid are all going to hit on you. 

This guy encompasses all five of those descriptions, and, sadly,
I've been out with him more times than I have time to count right now. 
Take screenshots of them and send them to your friends for entertainment. Or blog about them. Don't be mean; I'm not telling you to give out identifying information. But, like I've been saying all along, have fun with it. 

Are you ready to take the plunge? I'll write more of these posts over the next few weeks. There's so much more I have to share with y'all. 


  1. #7 isn't even close to being right. In the Pantheon of Really Bad Ideas, that one occupies a place of honor in the Dating Wing.

    Plenty of men will ask you out, but sometimes men are intimidated. Perhaps the reason he keeps returning to your profile is that he rates you highly - so highly that he suspects that you're out of his league. It might be that he's trying to get your attention and show that he's interested without having to deal with direct rejection from someone he likes very much.

    He's hoping that you'll make the first move. And if that's not how you roll, okay. But you might be missing out on someone great.

  2. Ha! I agree those images are creepy. As an online dating coach, I totally concur that you shouldn't expect or assume you'll meet your future husband or wife... but you never know! I met mine online, and now I have a business helping people navigate some of this craziness. :)

    Your take on modern date payment etiquette may work for your demographic, but for plenty of women it's totally appropriate to foot the bill. And for some women, it's also appropriate to be the date-asker. I don't blame you for writing from your perspective, but I don't want your readers to be afraid of trying out other strategies, especially if your advice isn't working for them.

    Feel free to track me down at for loads of free online dating advice and resources, or if you'd like to hire me for personalized coaching. Good luck out there, lovebirds!

  3. @Gaul Soodman First of all, lurv the name. Okay. In my experience, asking out dudes doesn't work. I've tried. Oh believe me, I've tried EVERYTHING. And for me, most guys are going to be intimidated from the get go because I am taller than most girls and have big, red hair. The ones who aren't intimidated are the ones I've liked the most. I'm 32 now, which means I'm past the experimentation years. I tried. It didn't work. And most girls I talk to say the same thing. I don't know who you men are coming out of the woodwork saying you like it when girls ask you out! Where have you been all my li-i-i-i-i-i-fe?

  4. @Virginia Roberts Thanks for adding your perspective! This is why I prefaced the post saying I think I'm an expert on staying single. However, for the record, I didn't say you wouldn't find your future person online, I said CHANCES ARE you won't. That means you might. I am not bitter, just keeping my expectations low so if I do meet a great guy online, I'll be ecstatic! In the meantime, the footing the bill thing is totally up to whomever wants to do it. I just wanted to give my readers my permission (that counts for nothing, mind you) to not do the awkward reaching for the purse thing at the end of a date.

  5. As someone who has gone on a date with you. I appreciated the awkward reach and that you said thank you when I paid the check.

    A good guy will not mind picking up the check, but it's nice to be appreciated and not be looked at as another free meal.

    I know you are nicer than the tone of this post.

  6. I haven't dated online but I agree with your opinions totally. I think of myself as a modern grown up woman but I'm not wasting my time chasing and asking out men either. I believe if a lady is interested, give him a signal that he won't be rejected then let him ask. I don't care how many men may claim to be too intimidated and like it when a woman asks them out, in my experience if he's interested enough he'll find a way. And if he's not, I'm not shaving my legs for that :)

  7. @Anonymous Geez now I'm dying to know who you are!!! And I feel like maybe we should have gone out again. :( I feel bad. Okay I just amended this post.

  8. Oh my comment got eaten! Just wanted to say I agree w/ no asking out either - for me personally at least. In my experience if a man is interested enough he'll get the digits. And if he's not that interested I'm not wasting my energy chasing him. If I'm interested I'll try to give him a signal that I won't reject him b/c I respect how nerve wracking it must be. And dudes paying: he (or she) who invites pays. Never thought of an invitation in this way until I was out with a male friend in Europe and I tried to pay for something and he said slightly offended "But I invited you!" and it wasn't even a date. He used the English word in a way I'd never thought about. To me that's classy and I would feel bad to step on the toes of a man who asked me out and then attempts to pay. Dear blogger is this a southern thing? Of course a lady always says thank you for the date. Anecdote: I had a boyfriend of far greater means than me who paid for almost everything for the entire 5 months we dated and I could tell he liked being able to do that and he was awkward if I tried to pay so I let him and didn't feel bad about it.

  9. Oops just realized comments aren't posted immediately!

  10. First of all, I loved the post, and want to say that I took it as more tongue-in-cheek than anything as I know what a great person you are!

    Second, I just want to offer my agreement with #7. I used to be the one telling all my friends to just go ahead and ask him out, but it DOES. NOT. WORK. Every single time I've tried it online, it doesn't work out.

    Plus, I agree with you, I'm going to be more interested in the guy who isn't afraid to contact me in the first place, so I'll sit here and paint my nails while I wait to hear from him, thankyouverymuch.

    Such a funny post! More, please!

  11. Re: asking guys out - I don't agree with Gaul Soodman. I've got no explanation for a guy checking out a girl's profile over and over and not messaging her, other than he sounds like a pussy. HOWEVER, I don't think there's anything wrong with a girl sending the first message on an online dating website. Just start the conversation. Let him ask you out if you don't want to make that move, but go ahead and fire a message if you're interested. If he likes what you say and what he sees, there is nothing negative about that.

  12. I apologize for engaging on twitter where one's point can get distorted by character limits. As someone who has never little a girl pay on the first few dates and is happy to spend money on someone I like, I don't consider myself cheap - which is why I guess your post rubbed me the wrong way.

    Regarding the paying and types of dates:

    I'm not going to delve deep into the fact that the world we live in today is not the one you were raised in and that it's basically not possible to go to dinner in DC and have a coup drinks without dropping $150+. Our parents/grandparents were raised in a world where black people had to sit in the back of the bus. Shit changes.

    Based on your amendment and Anonymous' comment I understand you to just like the chivalrous concept of a guy taking you out and paying for you. I don't think you are some mooch looking for free dinners.

    However, hopefully more eloquently than I could deliver on twitter:

    It's online dating. You're both meeting a bunch of strangers hoping you find one you like. There are a lot of swings and misses. For both men and women. People are busy, and things are expensive. Asking a girl out for drinks as a first date is a calculated decision. A few messages exchanged online is enough to decide someone is worth meeting, but until you meet them you have no idea if they 1) are who they represented online or 2) if you are interested in them. Why subject either of yourselves to more than a couple drinks without knowing that? If you have a good time, and both parties are in for a second date, then go to dinner. Or a 1st date can evolve into more if it's going really well. It isn't about being cheap, it's just being practical. It's a test.

    So the attitude that "you've held up your end just by going" and "order whatever and don't feel bad" doesn't sit right with me and I promise you it won't sit right with most guys. I will not improve your chances finding someone.

    My one piece of advice is simply to treat the date like a mutual investment. He won't mind paying, and most guys will (I don't know of guys who don't insist they pay on the first couple dates?), but the attitude of "I'm excited to meet this person and willing to put my time/money into it" vs the attitude you described does come across and does impact how the guy will feel about you and the date.

    If that falls on deaf ears, so be it. I will now uphold my promise and go to bed (and not tweet you again).

  13. Thanks for the follow-up, Mary El.

    You run a blog where you say that your ideal man "will never ever let me pay for dinner," ..and then you're surprised when men say no when you ask them out to dinner?

    Every stop to think that the two might be connected? Ever suspect that a man might be put off by a woman who's essentially demanding that he buy her a meal?

    I've been asked out by plenty of women. Sometimes it's coffee. Sometimes it's drinks. Sometimes it's a meal. But the answer is never "yes" to a woman who comes across as trying to get free shit.

    We eligible, decent single men are not unicorns, Mary El. We're not mythical fantasy animals who were put here to fulfill your dreams and do your bidding. We're human beings with moral agency, and we don't like women who reduce us to ATMs or force us to adhere to arbitrary rules.

    I'm pretty sure that you're a good person, but my goodness, your blog persona is a gold-digging toothache whose happiest moments center around getting expensive stuff for free. What eligible man wants that?

  14. @MitchRapp Thanks for clarifying. I hear you. What is coming up in the next post on this subject is for most of us girls, to takw on tjis attitude actually just moves the dial of how bad we feel a little. I'm not suggesting anyone abuse anyone, but as a girl, guts have been disrespectful to me on dates maaaaaany many many times. So this post was really more if a pep talk than a manual. I didn't communicate that well. Good on you for pointing it out. I think you can be far less abrasive next time you want to make a point. You will be heard quicker and better if you behave nicer.

  15. @Gaul Soodman Read the other comments dude. Anyway, the girls get it and the guys are offended. Shicker. Y'all are taking this the wrong way because I didn't write it for you. I don't need to gold dig -- I do quite well on my own! And no, the two are not connected, because no guy I've asked out on a first date has ever said yes. But you hit on a good point, it's my blog persona. Civilized people know to take this stuff with a grain of salt. So calm down. It's satire, it's a pep talk to girls, and its sole purpose is to make my fellow single ladies feel not so hopeless and alone. And you guys? Are part of the reason I have to write posts like these in the first place. You and Mitch and your nasty comments...I heard from several other guys tonight that expressed your same sentiments in much more gentlemanly ways. Congratulations on justifying everything I wrote in this post.

  16. Oh, it's satire, is it? I get it. You didn't enjoy that $280 bottle of wine. And I guess you weren't actually upset about getting dumped, either. Just more zany satire from DC's female answer to Jonathan Swift.

    Back here in reality, you meant every last word. And that's why no men accept your invitations for dates. Seriously, I've never heard of a 0% success rate for someone who isn't hideous. What you're experiencing isn't typical, and it's all on you.

    1. Sure I enjoyed it, and the man who bought it was happy to splurge because we were having fun. And of course I was upset about getting dumped. I'm not understanding why you've taken it upon yourself to be an ass all over my blog. Again, the girls get what I wrote. What I'm experiencing, and have experienced for years, aligns with the experiences of the majority of the women I know. I'm not hideous at all, and neither are they. I'm all for a friendly discussion of topics, but you have taken this too personally and too far. I suggest you go read a dude dating blog and get over it.

  17. I get the point of the blog post and that it's satire, etc. I really wasn't riled up or bothered upon first reading it - I just find that some of the attitudes expressed in the post are common among women and actually destructive to their very goals, as I expressed above. When I tweeted that I thought #6 and #7 were off base and was told I was cheap and an "asshat", I went from discussion to pissed and abrasive pretty quick. Not saying I take no responsibility for that, but that more was how it went down in my eyes.

    The main point I wanted to get across is that online dating has its issues for everyone and everyone goes on bad dates they wish they hadn't wasted their time and/or money on and rather than women feeling like they are alone on that and taking some of the attitudes you expressed, treating it with more consideration will likely yield better results.

    To me "have fun with it" should simply mean not taking it too seriously and expecting it to yield a spouse immediately, but that it's just a means to meet some people and see if you like them and if not, you both put in a little effort and came away with nothing, no biggie.

  18. Also I'm not sure why the fact it is a blog directed mainly at females is relevant. If I wrote a dude dating blog I'd want female feedback. Assuming there is any seriousness to the thought that at some point you (proverbial) want to find someone, getting input from the opposite sex seems like it may have value.

    And if I wrote a "satire pep talk" to guys about how to spend less and get laid more from online dating, I'd expect that feedback from girls to be negative.

    1. I'm just excited people are reading my blog! I stand by what I wrote. And I absolutely appreciate everyone's thoughts. The lashing out at me has been excessive, though, and a couple of yous have not bothered to see things from my point of view but rather made snap judgments basef on one paragraph. That's where I'm coming from, at this point.

  19. Wow. Some people need to simmer down a bit.

    To the people who disagree with Meppers, I think you need to understand that the South is still old school. Boys pay for dates. You don't go to college football games without a "date" (seriously, not a joke). Girls wear fake eyelashes every day. And a majority of women wouldn't be caught dead outside of the house without makeup and hair done. The stereotypes are true.

    And MEN ARE OFFENDED IF YOU ASK THEM OUT OR OFFER TO PAY. I moved there as a 6' tall women who had no fear in approaching men because... well that's just my personality. I can't recall at least 3 conversations with different male co-workers who were horrified and absolutely mystified when I told them I would totally hit on a guy in a bar, heck that's how I met my husband. They were literally offended and said they would NEVER date a girl who approached them "because she must be slutty". Which offended me because I am not "slutty".

    This is the perpective/history of the woman who wrote this blog. Yes it is different then yours and likely incomprehensible to you. Trust me, I know. I was the same way when I moved to Atlanta, but I also discovered the charm of tradition and that it IS nice to be considered a "prize to be won".

  20. @Anonymous 12:31-

    That's a nice explanation, but our host (1) isn't in the south, and (2) is talking about online dating.

    Maybe southern men don't want women to approach them, but that doesn't tell us why Washington men turn her down when asks. And maybe those same southern men don't want to be hit on by a woman at a bar, but they might be open to an online suggestion to go out.

    Ask DC men who have done the online dating thing. Ask them if being asked out by a woman is a negative. Ask them if they lose interest in a woman whom they already like if she makes the online approach.

    This assertion of a complete failure rate when asking men out doesn't match my experience at all, or those of any of my friends. If a man turns you down online, it's because he's not interested, not because you were too forward.

  21. LP,

    Again. Trying to provide some perspective on M's "culture". To disregard that as "she lives in DC now" is like saying that people from India who moved to America shouldn't have an accent, watch Bollywood movies or arrange marriages for their children.

    Guess what, arranged marriages in America do still exist. I know several happily married couples whose parents arranged their marriates. It's all about culture and what they've been raised to see as acceptable.

    My point is even if someone switches geographies, where and how you were raised for 28 years of your life (or more) still has an impact on how you view the world.

    To respond to "this is online dating" comment... let's go back to the algorithms part of the post. You respond to a questionaire that is supposed to get to the heart of who you are as a person. What your preferences are and who would be compatible, or something like that, right?

    Maybe this algorithm recognizes the whole "likes romance, chivalry, and being the prize" mentality. Maybe it doesn't match her with guys who are OK with being asked out because that's not how they answered those same questions? And maybe you're right, maybe the guys just aren't interested in her. But truth is, you don't know why either.

    Unless you work for one of those dating sites... if so, please explain how those algorithm/matching things work because I think there are many women out there who would LOVE to know. And I'm being serious here, not sarcastic. I think there are lots of people who can't figure those things out.

    Trust me, not trying to insult any commenters on here. But try to give a little leeway for the fact that these are HER experiences and HER perspective.

    1. @Anonymous I second your request for more info on those algorithms. And what a good point, I might add! This is all interesting, hopefully someone with insider knowledge weighs in. I'm doing some research in the meantime.

  22. @Lord Palmerston You bring up an interesting point -- if he's not replying it's not because I'm being too forward but because he's not interested. Can anyone tell us online lady daters, then, what interests an online gentleman dater? None of my friends seem to know. I've been under the impression that guys lose interest when I show it!

  23. This comment has been removed by the author.

  24. It's human nature that eagerness is a turnoff, and that goes both ways.

    But sending a message first, or even being the one to suggest meeting a drink, is not a turnoff to guys.

    I can't speak for all guys in terms of approach to online dating, but mine was fairly simple:

    1) am I attracted to your pictures and do I believe them to be accurate?

    If so,

    2) is there anything in your profile that is a blatant red flag that makes me pretty sure we won't get alone?

    if not,

    I'm probably going to be willing to meet for a drink and see if we get along. Now, if your profile is particularly funny or makes me think we have a lot in common, or your messages, that may spark my interest even more. But as long as I'm attracted physically and there are no glaring warning signs I'm probably interested in meeting up.

    I'm not too interested in going back and forth with messages forever, I'd rather just meet and find out in person which I think is a much easier way to tell if you like someone (which brings us full circle back to the point that I almost always go 1st date drinks rather than dinner).

    1. @Mitch Your approach sounds like mine, and probably most people's. I hate the going back and forth online!

  25. @Anonymous 05:00:00 PM

    I'm not telling her to do away with her southern customs. I'm telling you that if a man in Washington doesn't accept your dinner invitation, it's probably not because he's offended that you asked. This isn't Savannah or Baton Rouge. Chicks ask dudes out here.

    My entire point is that if a DC man doesn't accept your invitation, it's not because you've committed a social faux pas by asking. It's because he doesn't care for your face or your personality. He's just not that in to you, as they say.

    Bottom line: you gals must be asking super-hot, super-rich men out on dates. Because I won't turn down a simple first date from someone who's reasonable attractive and doesn't have any horrible red flags in her profile.

    As for the algorithms: algorithms, schmalgorithms. Every dating website I've been on has allowed for open searching. You can look at profiles of people whom the computer things are bad matches. Look at those profiles, and if you think the computer's wrong, make contact and have something interesting to say when you do.

  26. Online dating...meh. I'm not having the best of luck and it's really discouraging! Am I too picky? Well, I guess I should be. But, I don't think I am being.

    Great article!

  27. Hilarious! Time for me to join and experience this first hand ;)