20 Online Dating Tips: Your Guide to Cyber-Studliness

Many readers have written that it's tough to meet like-minded women, especially if you live in a small town or have a career that rarely puts you in contact with other women-lovin’ chicks!

When I was actively dating, I dabbled (okay, more than “dabbled”) in online fora, partly because Match, OKCupid, and Yahoo! Personals were quieter, less irritating places to meet people than in bars, and partly because I could pretend to be socially active while sitting in my recliner drinking a Fat Tire.  Although I didn’t find lasting love in cyberspace (though I made some great friends), I highly recommend it.  Here are a bunch of easy tips to get you started.  Some are written with butches in mind, but most apply to everyone:

1. On your profile, don’t put up the best picture that’s ever been taken of you.  If you do, then when someone actually meets you, there’s nowhere to go but down.
2. Meet people in person as soon as possible.  No matter how many pictures and emails you swap, there’s nothing like meeting someone in the flesh—you immediately get a sense of her persona (and whether there’s a chance in hell you’d ever want to wake up next to it).
3. Include fun pictures, but beware of subtle messages you're sending.  A picture with an ex CLEARLY cut out or blacked out = vindictive.  More than one picture that includes alcohol = hard partier.
4. Don’t plan long first dates.  No matter how awesome someone seems, or how articulate her emails are, you do not know her!  I made this mistake once.  S. and I exchanged four long, riveting emails, then made plans to have lunch, see a play, then have coffee.  Within five minutes of meeting this Yale-educated doctor(!), it became evident that she was the most boring person I had ever met in my entire life.  This woman was like a vacuum.  She was the anti-interest.  We went to the play, she laughed at all the stupidest parts, and I bailed on the coffee before she could kill me with her abyss of boredom.  Afternoon wasted.
5. If you're transitioning, say so.  My trans and trans-loving buddies tell me it's perfectly kosher to list your sex as "female," then explain in your profile that you're FTM.  Or, if you want to date gay men or straight women, you can list yourself as "male" to show up in searches, but again, you should specifically state that you're transitioning.  Saving the surprise for bedtime can not only be uncomfortable; it can be dangerous.  
6. Always meet in a public place rather than at one of your homes.  Tell a friend where you're going and with whom, and plan to have your friend call or meet you afterward. 
   
7. When writing your profile, employ tools such as spell check and fourth-grade grammar.  Personally, if I read something like: "If your intrestid in mebbe seein a moovie or whatevs hit me up," you can be assured that I most certainly will not.
8. If there’s a certain "type" you'd never date, say so.  This will prevent femme-loving butches the agony of sending doomed communiqués to femme-loving femmes, will save vegans the trouble of swooning over carnivores, etc., etc.  In general, it's nicer to say what you DO prefer, not what you don't—i.e., "I find tall women very alluring," is nicer than "Women under 5 foot 5 need not apply."  "Need not apply," in particular, makes you sound like a princess unattractively scrutinizing a long list of potential suitors.
9. Everyone likes "laughter" and "having fun."  Such trite descriptors should not appear in your profile.  No one thinks of herself as a mean person who likes to have a shitty time.  Statements like, "I enjoy having a good time and laughing with my friends," or "Message me if you’re a nice person who likes to have fun," translates to: "I have no hobbies and am not especially creative." 
10. Don’t conceal your body type, statistically improbable height, missing limbs, cartoonishly large eyes, or other physical "imperfections."  ("Imperfections" is in quotes because I do not believe such things are imperfections at all.)  Don't use a misleading photo to get date #1, then hope your personality will win her over in person.  If your appearance would have kept her away online, it’ll keep you from scoring a second date.  Besides, why date someone who doesn't think the real you is cute enough for a first date, anyway?
11. "LOL" stands for "laughing out loud," not "I am vaguely amused."  Thus, it is appropriate to write "LOL" only when you are literally laughing out loud.  Unless you are (1) a hyena, or (2) terribly ironic, do not write profiles or emails that contain sentences such as, "I can’t pick a favorite band cuz I love so many lol!" and "It was great to see you last night—I love that restaurant lol!"  Suggesting that you are laughing out loud, when you clearly should not be, will not cause your date to think you are funny; it will cause her to think you are nuts.
12. Be nice.  Our community is small, and even if you can't stand the person, you may end up running into her again!
    
13. Under your "self-summary," try to avoid statements like, "Too much to be summed up in 100 words!"  You’re a human being, so this should go without saying.  If you don't have time to write anything, save your profile and don't post it yet, OR write something sexy and alluring, such as: "I'll write more later, but for now, I'll simply say that main interests are office supplies, bingo, and goat cheese."  
14. Referencing your baggage reads like a cry for help.  This includes thinly veiled references to exes or past dates: e.g., "Please be over your last girlfriend for REAL and do not call her during our dates," or "Please do not have any weird daddy issues that you bring into bed."  (These can get eerily specific.)  It also includes people who have been helped by some form of therapy and believe they are now "fixed."  This ilk writes things like, "I have done a lot of personal growth work and am looking for someone who has gotten past their issues."  I can't pinpoint why I dislike this so much, but it's a complete turnoff--maybe because I doubt that anyone introspective would ever believe that she is "fixed" or done growing.
15. Have a close friend check out your profile and see if it seems like a pretty good summary of who you are, or if you're leaving important things out.  Your friends are your biggest advocates! 
    
16. Wear something nice to the first date.  This is location- and season-dependent, of course, but in general, a T-shirt, shorts, and flip-flips do not qualify.  A button-up shirt, khakis or nice jeans, and non-tennis shoes are a good bet.
17. No raw onions or heavy garlic.  Think about the goodnight kiss.
    
18. There's no good way to say this, so I'll just be frank.  If you sleep with a woman, she may assume you are now "dating," or even that you are now her girlfriend, even if you are completely upfront that this is not the case.  As such, I recommend not sleeping with someone on the first couple of dates [she wrote, brimming with honesty and hypocrisy].  If you do...  let's just say that all the "processing" that ensues afterward may make you regret your fleeting lack of self-control.  (And one more thing to think about: contrary to popular belief, AIDS and especially unpleasantries like herpes do exist in the lesbian community.  It pays to know what you're getting yourself into...  um, literally and figuratively.)
    
19. It's okay to call the next day, or to send an email.  Something like, "Just wanted to thank you for a really nice time last night.  I'd love to see you again sometime soon!" is totally appropriate.  And if you're the recipient of a note like this, know that it probably took a lot of courage for her to write it.  If you do want to see her again, make sure you SAY so; she may interpret a note that just says, "Thanks for a nice time" to mean that although she's nice, you don't want a second date.
    
20. Assume that a certain level of awkwardness will ensue.  Plan accordingly and give yourself a break if things feel forced at first.  After all, you’re meeting someone you don’t know.  You’re both putting yourselves out there—saying, "I want a relationship badly enough to seek it online, and I've already gone through my friends' friends, and nothing worked out."  If you end the night even a tiny bit interested in a second date, you get to chalk it up as a win!

What has been your strangest online dating experience?  Any tips to add to the list?  Any questions about things I haven't covered here?