Tips for Dating via Personal Ads

I’m trying this dating thing again, and I’ve answered a couple of personal ads on Craigslist in the last few weeks. No dates so far – seems the flirtation dies out pretty quickly, and frankly, I could pursue it, but I’m not willing to do all the work. Some, yes, but you’ve got to make it worth my while, you’ve got to pique my interest. I’m definitely more picky than I used to be, and I’m not so willing to compromise – hell, I’m not quite even sure I’m ready to date, I’m still dizzy from the ending of that last relationship with DD. I’m not in a hurry, but I am getting just a wee bit anxious to get laid.

Meanwhile, we’ve coined some new terms: DND, definitely not dating; email chemistry, for what kind of feeling you get from someone via writing; small-r vs big-R relationship.

I’ve noticed a few patterns in this dating adventure. Here’s some things that keep coming up for me. Got any tips for me, or for others? What have you learned by dating on the internet? Lay it on me, I can use all the help I can get.

  1. When placing an ad, make sure you have time in the next two weeks or so to go on follow-up dates. Clear your date nights – Friday and Saturday – or, if you can’t do that (if you work those nights, for example), have a few other options open, brunch on the weekends, or typical happy hour time for those who may be doing that 9-to-5 office thing. You don’t have to go out with everybody who answers, of course, but you want to be able to pick two or three of the good responses and be available to actually meet in the near future.
  2. When sending photos of yourself:
    a) ask your friends to help you pick out the shots that actually look like you, even if they aren’t what you consider to be your most flattering photo;
    b) include a shot of your face and a shot of your body;
    c) do not include photos of you with your ex. Have your friends take new shots of you if those are the only ones you have;
    d) resize your photos to somewhere around 600px by 400px. Attaching huge, giant photos directly from the camera is very inconvenient for the recipient, and are hard to see.
  3. Your social networking site is also a personal ad. Send on your Myspace/Friendster/Facebook site upon sending your name or your photograph (your potential date will probably Google you anyway). If you use your Myspace profile for something else (keeping an eye on your kids, connecting with your high school students) make a profile that just highlights you, where you can actually write things. No need to be smutty and intimate and TMI, just have it be an authentic representation of you. This profile should be PUBLIC, with some photos that you haven’t already sent onto your prospective date, because why else would we be looking at your profile? To gauge whether or not you are physically interesting & attractive. That doesn’t necessarily mean “conventionally beautiful” – it means, whether or not I’m intreagued by the way you look. If you need to keep this private, for whatever reason, then after your prospective date sends you a request to be added, please follow up on that quickly.
  4. When you set a tone in your personal ad, it’s best to follow up with that tone too. You created a persona for yourself in your ad, if you can’t follow through with it, best to put up a persona that you can follow through with. Sounds cheesy to say “be authentic,” but, come on. Be authentic, even if that authenticity is NSA dating & sex. That’s authentic too.

Published by Sinclair Sexsmith

Sinclair Sexsmith (they/them) is "the best-known butch erotica writer whose kinky, groundbreaking stories have turned on countless queers" (AfterEllen), who "is in all the books, wins all the awards, speaks at all the panels and readings, knows all the stuff, and writes for all the places" (Autostraddle). ​Their short story collection, Sweet & Rough: Queer Kink Erotica, was a 2016 finalist for a Lambda Literary Award, and they are the current editor of the Best Lesbian Erotica series. They identify as a white non-binary butch dominant, a survivor, and an introvert, and they live outside Seattle as an uninvited settler on traditional, ancestral, & unceded Snoqualmie land.

8 thoughts on “Tips for Dating via Personal Ads”

  1. Dev says:

    My advice after doing this for a few years is "Meet sooner rather than later." It's easy (for me) to get caught up in a series of epic emails, then meet and have everything fall flat. If you're hoping for a real-life relationship, move it to real life soon.

  2. roro says:

    Excellent tips, particularly the "be authentic" part. I would add that instead of simply using words like "smart, funny and sexy" to describe yourself, it's more effective to actually write something smart, funny or sexy.

    I posted a few other online dating tips on my blog awhile back – I think most of them are still valid. Hope your online search is fruitful – looking forward to reading about it!

  3. Jackt's girl says:

    This is exactly how I met that hot butch in the previous post (thanks for posting the picture – I love to be reminded of what a lucky femme I am).

    Here is one of the many magic ingredients that worked for us.

    Be specific. About who you are and what you are looking for. The specifics we listed in our profiles made it abundantly clear that we were starting out with a lot of potential for compatibility. After sifting through a lot of profiles I noticed that most people make their profiles as broad and vague as possible, in order to attract more people I presume. I figured specificity was an effective way to weed out the potential responders who were not going to be into who I really am or what I was actually looking for. I still got a lot of hits and flirts from people who clearly did not fit what I was asking for, but it helped steer me and my sweetie toward each other.

    We met each other on the personals site which seems to have a fairly high success rate. Have you ever tried that site? I seem to remember lots of folks from NYC on there.

    Well good luck with your date search. I find it difficult to imagine you’ll have much trouble getting laid once you put your mind to it :).

  4. I’d also say that being authentic in your profile is helpful. I can tell when women write their profile according to what they think others want to read. Honesty is best; I’ve found plenty of people who like all my little quirks.

  5. saintchick says:

    Love all the pointers that are listed. What I did was ask a couple of my friends to give a little tidbit about me. I didn't agree with all the comments ( bossy & stubborn) but I still used them. So far no problems !!

  6. Zoe says:

    I agree with Dev about meeting sooner than later…otherwise the whole thing is too middle school.

    Also, I think it's helpful to include something in the ad that the reader can respond to, like a question. It might be a little cheesy, but it also helps the responder right something more interesting than "your post caught my eye…"

  7. SuperSoftStud says:

    what sparked a robust and really great round of internet/cl dates for me recently was an ad that listed out some of the specific types of dates that i wanted to share, i was specific about the activities that i like and some were silly, some serious and some sexy….that has gotten alot of responses. and dev and zoe nailed it. i will never again do the epic, pen pal e-mail thing. i agree with you, if you can't meet me in the next two weeks, then you probably don't have time to date!

  8. LataneBlu says:

    I can't understand why women spend so much time selling themselves on their SEX appeal mainly. I'd like to be able to have my mind stimulated as well with conversations of substance.

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