Relationship Ramblings

Advice for the Guys: Chatting it up with the Ladies

Dear Trollers (I mean this in both the most respectful and damning ways, depending on whichever way you roll),

Speaking for the Internet’s sexiest women, we get it. You love sex. That’s why you’re cruising the dating sites, lurking on the erotic message boards and in the chat rooms, and viewing and downloading porn videos and pics. Sometimes you come across a woman you think would be hot to chat with or even meet for a hookup.

I’m not saying what you’re doing is wrong; it’s just that a lot of you are doing it wrong.

First of all, get a good idea if a woman is open to some hot erotic chat or a hookup. Don’t assume that every woman in these places is looking to get her freak on or is an on-demand porn bot. Some women like to go online to lurk at these sites privately and discreetly. Some are happily married or otherwise involved. Some are looking but are only looking for a Prince Charming with a pervy side. Just because some women are curious about or enjoy or embrace their sexuality doesn’t mean they’re putting themselves out there for you.

If possible, publicly ask for permission to send her a private message or email. Sending a suggestive message out of the blue, especially if she has no idea who you are, is often considered the same thing as barging in her bedroom. “Knock” politely first before you start talking about wanting to take her clothes off and ravish her.

If or once you get in her inbox, start off with conversation. Let her know why you’re interested in talking to her aside from just you being hot and horny. Mention something the two of you may have in common … besides interlockable body parts. A one-line listing of your vital statistics and a request to “tell me more about yourself,” especially if it’s littered with grammatical and spelling errors, is not a conversation. Even if you have a raging hard-on that demands immediate attention, manners count and manners are sexy. If it’s a sexual emergency, download some porn, order some pay-per-view on cable, visit a pay site, call a chat line, or call a pro. Don’t make your “problem” some random woman’s problem to spend her time to take care of. It’s not that women aren’t caring people, but you’ll survive. No one has ever been hospitalized for or died from a case of blue balls. If have an erection that lasts more than four hours, like the erectile dysfunction drug ads say, get yourself to a doctor or a hospital.

If you’re disappointed or get pissed off if a “woman” replies back with a link to a pay site, consider what you’re looking for.

Be as upfront about your intentions for getting in contact with her without being vulgar or graphic. Let her know if you’re looking to chat just one time or if you’re looking for someone you’d like to get to know on an ongoing basis. If she says, “No thanks,” or doesn’t reply, move on and respect her wishes. Getting pissed off, calling her names, hounding and begging is very unattractive, if not creepy, immature and/or douchebaggy.

Be honest about your relationship status. Often times being married, involved, or “just dating” is a deal breaker. Sometimes it’s not. Lying about it is wrong. Furthermore, “separated” does not mean that you and your significant other sleep in separate beds; it means a divorce is pending and that the two of you live in separate residences. It does not mean that you plan on divorcing your wife once your 6-year-old turns 18. (I actually had a man tell me that years ago.)

We also get that men are visual creatures. If you really need to see a picture of a woman you’re chatting with, send yours first. If it’s your requirement, play by your own rules. It’s only fair and reasonable that she can judge whether you’re worthy of conversation, too. Plus, many women value and guard their privacy. Send a picture of yourself that’s similar to how you present yourself in public. Make sure it’s current, that it’s a picture of you, and by all means, don’t send a dick pic. It’s not considered a good first impression.

Also keep in mind that men outnumber women in online sex spots by three to one under the very best circumstances. If she just put up a personal ad, chances are that she could have as many as 100 emails awaiting her attention. If she’s been a member of a site for quite a while, she probably gets a message from a guy like you at least once a day. While electronic communication is immediate, never expect an immediate reply.

If you’re looking for just a one-time local hookup, tell her. Don’t deceive her by playing the nice guy routine just to advance your agenda. Once she catches on, she’ll have every right to get pissed off. If she’s crazy enough, she’ll track you down and find you … or have a bigger, stronger and male friend track you down and find you … or have a couple of tough, butchy lesbians beat the shit out of you when you least expect it. (I know someone who can and has made these kinds of arrangements, although not for me.) If she’s a lady who will suck up her error in judgment in silence, she’ll be hurt. She’ll probably hold back on that real Dream Man who wants to swoop her off her feet. Even if you have no conscience or sense of empathy or remorse, just know it’s wrong and bad. You’re an adult. Act like one.

I know this was a lot to read, but please don’t consider this a waste of your time. The biggest waste of your time is repeating the same mistakes over and over and never or rarely getting what you want.