Rules for dating when you actually want to date.

In a recent comment discussion with a fellow blogger I got to talking about my online dating rules…and figured I should write them down. It helps me stick to them, and I’m curious what everyone thinks.

I didn’t start off dating this way. My priorities were different – have a LOT of sex, feel wanted, reinforce I was attractive to men, and explore dating in all its forms. I succeeded, and it sure did garner a lot of learning and stories for this blog. If you haven’t read my old stories, you can find them on my “men I’ve slept with” page starting at #38.

Two years ago, I didn’t want a serious relationship (I also have a blog post in my head about my definition of “serious”). I didn’t want to be exclusive. But I did want to date – meaning go out and do different things with men I like. More than just the euphemistic “hanging out” at my place.

I realized it’s very difficult to find men willing to put the effort into dates when they aren’t actually interested in having a girlfriend or a relationship. This was a big learning for me and I think it’s something that many of us haven’t really figured out. I could write a whole post on the reality of true “friends with benefits” opportunities.

After I came out of my relationship with Johnny Id last September, things shifted for me. While I was still very much on a journey of sexual exploration, I no longer wanted to deal with the idiocy of engaging with men who aren’t actually on the same page as I. Or who didn’t have at least the potential to be.

There is no middle ground for me now – it’s either engaging specifically for sexual exploration, on a site like FetLife, or pursuing someone to date with the ultimate goal of having a boyfriend, should the right guy come along. I’m not going to settle just because I now know I want someone in my life.

Different priorities means a different approach to online dating. It made a difference last Fall, when I met Tony, and I hope it makes a difference again.

It does mean I’m not engaging with a ton of men at the same time – things are slower – but that’s okay. Having a bunch of men in the “stable” just leads to confusion and dumb mistakes and an ability to really focus on people. I know I missed out on some good men in the early days because I was too busy sexting and communicating with others.

Here are my “rules”.

Rules about messaging on online dating sites:

  • Don’t reach out to men first, no matter how great they seem. If they like me, they will message me. While this seems archaic, I also prefer men who are confident and bold, so it’s a good way to weed out those who won’t go for what they want.
  • Ignore any messages that come from men who don’t meet my key criteria. The exception would be someone who is exceptionally witty or sweet with their opening message – then I compliment them on their message but say I think we are looking for different things.

My key criteria: 

  • Between the ages of 35-55. Yes, I increased my age range. I’m done with immaturity.
  • They can’t be long distance. Why bother?
  • Their profile must say they are looking for a relationship. Sadly, I find “dating” has become a euphemism for “hanging out”, which is in itself, a euphemism for “having sex at your place after I will show up empty handed”.
  • On POF if it says “not looking for a relationship or any kind of commitment” I say no, no matter what. 
  • On OK Cupid the match percentage has to be over 70% and they can’t be more that 20% enemy. The site was created by a statistician and the results are meaningful. Unless they’ve answered few questions…then the other criterion have to apply.
  • They have to have put some thought and effort into their profile. If it’s empty, forget it. If it’s obviously written on a smartphone and is rife with spelling and grammatical errors, forget it.
  • I really can’t contemplate dating anyone under 5’10” (my height). Perhaps shallow, but it’s my only physical criterion at this point.
  • I will really look closely at anyone who isn’t divorced: the reasons should be obvious, given my experience with Tony.
  • Their longest relationship has to have been around 5 years or more. If they are in their 40s, it should be higher. I’m pretty sure if you haven’t found someone to put up with you for at least that length of time, there’s a good reason. This isn’t a hard rule for me, but they have to have something in their profile that speaks to why they haven’t had a significant long-term relationship.

Rules about contact:

  • If they don’t ask to move to text after several messages back and forth, I stop responding. OR if we are texting and don’t ask to meet, I stop responding. Why? At the core, I think men who do this are either too insecure to meet, OR it’s because they have too many women in rotation and are keeping me on the back burner until they have an opening. Either way, I’ve found when the texting just goes on and on…it never becomes anything more.
  • If they are infrequent in their contact, I don’t try to get them to respond by texting again. Generally this means they have lost interest, or someone else has gone to the top of the pile. Either way, I’ve learned that most men will respond if you proactively reach out, but it doesn’t actually mean they are super interested. I wrote a post about this ages ago called “Truths we prefer to not admit“.
  • I will not engage in sexting with anyone I haven’t met. If they start to talk about sex (rare, given the criteria above), then I know it’s all they want – regardless of what they say. I may still be open to a sexual exploration with them, but frankly I’m more comfortable with someone from FetLife because I know exactly what I’m getting into.

Rules about first dates:

  • The first meeting has to be a coffee or a drink after work. No dinners, no late night meetings. I had too many bad experiences where the chemistry was awful and I was stuck in a dinner. I also know that given my libido, it’s much easier for me to decide “oh what the hell, why not take him home and have sex with him” if it’s late and I’m lubricated with alcohol.
  • If a man recommends something more extreme for a first time meeting – like a trip away or something that’s all day… it’s a HUGE red flag for me. Mature men who are also experienced daters know that chemistry is important – if they are willing to forego that, then there is something else going on and I’m unlikely to like it.

How I think about dates before I meet someone:

  • I no longer let myself get carried away thinking someone is going to be amazing. Perhaps this sounds cynical and sad, but the truth is until I’m face to face with someone, I just don’t know what kind of chemistry we will have. Too many times we were great on the phone or by text and in person it just wasn’t there.
  • I don’t get carried away with crazy texting all day multiple days before I meet someone. It’s too much mental and emotional commitment before we meet. I keep the communications to a reasonable pace.

What do you think? Are these too harsh? Reasonable? Do you think you are a fantastic catch and I would eliminate you based on these rules? 

[EDIT: I completely forgot another rule. I’m not going to have penetrative sex with anyone on the first date. I might try for the second as well, but don’t want to set myself up for failure…]

48 thoughts on “Rules for dating when you actually want to date.

  1. I think this list is great and well thought out. Job well done! Do you ever go on dates with people you meet on the street, at a bar, or that type of thing? You seem like your strictly looking for a online match, I just wonder why?

    • And thank you for always putting a link to the history of something you explain in a post. Makes for great reading while giving the reader, me, a better understanding…

    • I would gladly go on a date with someone I met in person, but it doesn’t happen all that often. Nobody I have asked knows any man they think would be a good match – one male friend said “all the single men I know are assholes”.

      Reality is I don’t go to bars to meet men…if I go its for dinners / drinks with friends and I am rarely approached. In some ways, in person you can gauge chemistry but really nothing else about the person. Online dating gives you the opposite – lots more information about them, but it’s a crap shoot whether you like them when you are nose-to-nose.

    • Thanks Hollie!! They definitely come from all the experiences I’ve had, and any time I think “oh I’m sure that doesn’t apply”… it does. I think I have a statistically significant sample size 😉

  2. 🙂 Great post honest and fascinating and all the stuff dating sites DON’T tell you, glossy adverts and veiled promises but truth is I’d never be a success. Can I say you’re both completely realistic and harsh but that’s no criticism, I want nothing more in the world than a genuine female relationship, so much so it hurts emotionally and taking it’s toll sort of physically lol I lose the will sometimes, out with the violins :)) but I have a strong guess on-line isn’t the place for the shy quiet insecure type, but that’s fine and something I’ve known for quite a while, people seem to assume that on-line dating is for everyone! Bullshit, like anything in life it’s a form of dating tailored to certain type, Like I said absolutely fascinating and I’m not being sarcastic annoyed or angry 🙂 l really did enjoy. Xx

    • I’m sorry to hear that it’s taking a toll on you, but I can certainly understand how that happens. Dating is difficult and it is filled with rejection and let down.

      BUT I think being online is a great place for shy quiet and insecure types, because you can put together a really great profile that speaks to who you are, in a way that you may not get a chance in “real life”. But you do have to be willing to reach out to women online – but unlike in-person, usually the worst thing that’s going to happen is she doesn’t respond. But you can reach out to 50 women in an evening if you like, which is really hard to replicate anywhere else.

    • I most certainly try to! Otherwise, I just stagnate… key is taking the learnings and putting them into action. Which I’m doing again, which is great. It really does make a difference.

  3. Just starting online dating, again. I’m going to try to use these. The only one I’m struggling with is the one about not contacting them first. I’m the type of gal that (used to) go after something that she wanted. But that hasn’t worked real well for me… I’m going to have to think about that. Lol

    • I am totally the same and it feels VERY weird for me as generally I think women and men have an equal role to play in demonstrating interest and moving things forward.

      What I can tell you from my own experience however is I have an incredibly low response rate when I reach out first.

      I think it’s more a feature of the fact that when online, men (and women) are engaged with multiple people. When a man takes the time to reach out it signals he’s ready to actually talk to me, and there’s no question he’s interested – two pretty fundamental criteria. When I reach out first, if he’s not ready, then it’s less likely to work. Then I just feel ignored.

      So on POF I will add someone I like to my “favorites”, and on OKC I will let them know I visited…but other than that, I don’t reach out.

  4. This hardly harsh, Ann. I would call this merely the product of learning and adapting and being mindful of your own feelings. At least you have given a lot of thought to this. I wonder how many guys have rules that are being the “she must, at least, be breathing.”

    Now that you have these fairly well-baked in the oven of experience, how will you adhere to them? What is your plan for oversight?

    • I know many people would see some of these as harsh, as a few are 100% black or white – I won’t make exceptions. But they are very much, as you say, grounded in my experience and I have yet to be proven wrong.

      I started adhering to these last fall when I went back online again, and I’m doing the same again. These aren’t rules that are hard for me to follow – and if I make an exception at least I’m aware of why (a particularly mature 33 year old, for example) and I think about it before I respond.

        • Of course there are immature 55 year olds, just like there are very mature 33 year olds. I do make exceptions, but there has to be something pretty great on their profile at either end of the range.

          I don’t know that I’m looking to be protected as much as I want to not waste my time. Online dating can take a lot of time as it is, and I don’t want to have this be all I do, so I want to ensure the time I spend is as worthwhile as it can be.

  5. Great advice and well thought out. Just stick to your guns and good things will come to you. I’m sure that there is someone out there who complements your feelings and desires, who you can be happy with.

    • Thank you Larry. I absolutely believe there is someone out there who is a good fit for me!! These rules help me ensure that I’m not wasting my time with those who aren’t.

  6. This post was excellent Ann, so much good advice. The one that I really take home with me is the one about letting the man contact you. While it may sound a little out dated, it is so spot on. Everything you have said here, I totally agree with!

    • I’m so glad you liked it!! I realized I’d learned a lot and wanted to share.

      The one about contact was one of the hardest to really internalize – and it’s entirely different from if I was in person. If there’s a guy smiling at me in a bar, I will most likely go up and say hello. Heck, you may even remember when I picked up the cop that pulled me over for speeding!!

      But things are just different online.

  7. I think they all make perfect sense and is not at all too harsh – in fact, your rules are even a bit more lenient than my own. For example, I won’t give someone my number until after I have met them and decided to have a second date. The reaction to that has been interesting. Some guys are totally fine with it – and others practically throw a fit because they think they should be able to get an immediate response from me when they want it. I feel like telling them, “Listen, my life does not revolve around you. I don’t even KNOW you yet.” Needless to say, I decline to meet those guys. I don’t need any controlling assholes in my life.

    • I think that’s an *awesome* rule, Jana. I’ve found some men’s sense of entitlement fascinating (and highly annoying). It goes along the same lines for me as men who labelled me “high maintenance” or “dramatic” when I would call them out on their bullshit or bad behavior. It’s a wonderful defence mechanism and tells us so so so much about their personalities.

  8. I don’t think these are harsh. They are the things that you know you want or that you know you cannot do without (or the opposite, that you cannot stand). Obviously, these rules may not work for everyone, but the idea of everyone writing their own set of rules is a very good one, I think!
    I have never tried online dating, and am not ready to start any time soon. I prefer the face o face interaction, the good old “We met in a bar/on the dance floor”. But I do realize this isn’t easy for everyone, either because men don’t reach out (like with you) or because they are too shy/insecure to go out by themselves.
    I am a party animal, and I don’t have the energy to throw parties any more (at least not at the moment), not to mention the fact that all my friends are taken… I need to give other men an opportunity, if I want to meet someone!
    I completely understand the ‘no late night date’ rule. I know that I have a similar problem. So now, my own rule would be ‘no first meeting sex’. At least, that gives me some time to think things over and wonder: do I really want to meet this person again? Do I want to sleep with them?
    Right now, I don’t mind meeting new people, but I realized I’m not really ready to take it any further… sigh!
    Good luck with the dating Ann!

  9. Excellent rules, excellent advice! And, though it does seem “old-fashioned” to let men contact a woman first (something my mother taught me), I think this advice is spot on. Men are wired differently than women, and so I think their making first contact is a sign of (hopefully) genuine interest (as opposed to “what the hell, I’ll talk to her”).

  10. I follow almost all the same rules! Since starting to date after my divorce, I have added:

    -always meet for a first date (no thanks on getting into a stranger’s car!)
    -no daytime Starbucks dates. They’ve never gone well, and men who can’t find a cool indie place probably aren’t a good fit for me.
    -call me on the phone to finalize plans before the first date. This is not only a screener but also so I’m not stood up, as has happened more than a few times.
    -I take a pic of their license plate and drivers license before I get into a car on the second or third date. Then I send it to my bestie. I feel safer this way.

    Thanks for sharing your list! I also automatically swipe left for a blank profile on Tinder. I need a little effort.

    • The car rules are definitely a good idea, but I didn’t add them because it’s not as relevant for me given where I live. I rarely drive to my dates, because I take public transit or taxis. But for sure, I think it sounds like you are taking good precautions.

      With regard to daytime coffee dates, I actually like them because I can often squeeze them in between meetings, thereby not prolonging the need to text someone for a long time before meeting them. And I like that I have a built in excuse to leave relatively quickly if I there’s absolutely no connection.

      What made your coffee dates bad?

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  12. We do the same thing when we meet up with a new couple but typically get together for a drink at a quiet bar. That way if there is no connection, we can simply bail.

      • For us we are not hard core partiers and if we can’t carry on a reasonable conversation with them, there has to be some major physical attraction there. Plus it’s been our experience that you rarely find a couple that both of you are attracted to both of them. If they look like they’d be a decent fit in our crowd, for us the next step is typically to invite them to a house party. That way we don’t have to “swap” which wifey doesn’t like to paint herself into a corner. For me the best thing to do is wait to see if she likes the guy or girl and make my move after she makes hers. But at a house party you don’t have to get with the other half unless you want to.

  13. I think everything there is very reasonable, although as a 5’9″ guy who ticks off pretty much the rest of the checklist I guess I’d be bummed about the height requirement. 🙁

      • That’s nice to hear. It’s funny, in all my dating and relationship life prior to online dating I never gave a second thought to my height. It was only when I was thrust into the online dating world that suddenly it became an issue for a surprising number of women. Anyway, it’s always encouraging to see someone who is able to separate preferences from dealbreakers. All the best!

        • I think part of it is we are reduced to statistics and measurements… I mean, I hate to say I have an “average” body time, because I think I’m sexy and while I have junk in the trunk there are other parts that are lean. But now that someone can search for “fit” or “athletic”, why search for “average”?

          Same for height, I think. The man I call “faraway lover” on this blog was 5’7″. I would never have responded to him on an online dating site, but he hit on me in real life and was an amazing lover. In person made a huge difference!!

          And thank you – you as well 🙂
          Hope to see you around here some more!

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