If there’s one thing I’ve learned from being on two online dating sites, it’s that there are a lot of men out there who have no idea how to talk to or woo a woman. So here’s some advice:
1. On a date or in any kind of communication exchange (instant messaging, cellphone conversations, texting), don’t bore her by talking endlessly about your own political views, relationship problems with your father, your job, and whatnot. Remember that the conversation has to go both ways. That means that you should NOT be doing all the talking – no matter how fascinating you think you are. Instead, ask her questions and take an interest in what she has to say. What are her favorite seasons? Does she like her job? What’s her opinion about the Tea Party? What are her hobbies and interests? Be inquisitive.
2. Similarly, when you do talk about yourself or your views, find a way to turn the conversation back to her. So, for example, if you’re explaining how much you love Vietnamese food, follow it up with questions about her favorite ethnic foods. What restaurants does she like to go to? Then when she tells you, enthusiastically suggest going there together sometime.
3. Say her name frequently when addressing her. This is very sexy and disarming. So, instead of asking, “When can I see you?”, say instead, “So, Monica, when can I see you?” Simply inserting her name into the conversation shows you’re taking an active interest in who she is and elevates the exchange to a more personal, intimate level.
4. When sending her a message through an online dating site for the first time, do not ever send her a generic introductory message that you send to all women. No canned speeches, please. It’s immediately obvious that the message is not personalized and that you just copy and paste the same message over and over again to hundreds of women. Yuck. Instead, write something brief that shows you actually took the time to read her profile and find her interesting. For example: “Hi Monica! I’m a big fan of film director Paul Thomas Anderson as well. In fact, my favorite movie is BOOGIE NIGHTS. What other movie directors do you like?”
5. Other miscellaneous online dating tips: Don’t forget to give her your real name if you’re messaging her on an online dating site. It’s incredible how many men forget to do this. You should leave your name in the first or second message you send her. Also, actually give a shit about the pictures you put up of yourself. Don't post the picture you took with your 2 megapixel camera phone in the bathroom mirror. Instead, post pictures of yourself in a variety of settings and situations to show you're a versatile guys with a social life. That includes pictures of you with friends, at a wedding in nice attire, shirtless on the beach, playing with your nephews, cooking in the kitchen, etc.
6. Never underestimate the power of texting. This is a great way to touch base without being intrusive and to let her know you care. For example: “I just drove near your hood + thought of u. What R u up to now? Keeping busy?” What's especially nice about texting is that you can often have a real-time conversation, but with the added advantage of being able to say what you want to say with greater care. You'll always be putting your best foot forward. It's much easier to be smooth and winning.
7. Before saying goodbye after your first extended conversation (either via cellphone or texting), let her know that you really enjoyed conversing with her. And insert her name in the sentence. Example: “Well Monica , I really enjoyed our conversation. Really looking forward to hearing more from you. Please feel free to call me anytime.” Make her feel desired and appreciated.
8. Don’t be afraid to show your vulnerable, sensitive side once in a while. Relate a story about a beloved pet who passed away whom you loved and cared for very much. That way she’ll see that you have nurturing capabilities as well. You’re not just focused on the Chicago Cubs, the rising cost of gas, and your job.
9. Whenever you see that you have something in common, point it out enthusiastically. If she says she likes snowboarding and you do too, respond, “Me too! How cool that we like the same sport!” If she says she just renewed her membership to Match.com after a long absence and you did too, respond, “Me too! I just renewed my membership as well!” And if she says she loves the Beastie Boys and you do too, respond, “Me too! I’m so glad we have the same musical tastes!” You have so much in common, it’s practically destiny!
10. Almost all guys already know to indicate to the woman that she’s hot, sexy, beautiful, or whatever. Yes, it’s always nice to be addressed thusly: “Hey sexy, whatcha doing?” But it’s also nice to tell her that she’s sweet. Simply say to her, “You’re really sweet and that’s what I like about you.”
11. After you’ve been speaking to each other for a while or after the first date, show that you have at least some inkling about what makes her tick – this proves that you’ve been listening to her attentively and are perceptive and thoughtful. Say something that indicates you understand her. Examples:
“I saw a trailer for the movie Black Swan and it seemed like something you would like because you mentioned you really enjoyed Darren Aronofsky’s last film.”
“I know how much you like a bargain so maybe you want to go to this mammoth block sale that’s happening in my neighborhood this Saturday?”
“I can tell you’re pretty exhausted by the end of the work week so would you prefer to just stay in, rent a movie, and order pizza?”
“I bought you this perfume you like because I saw you were running out.”
“I know how much you hate loud crowded bars, so maybe we can go to The Abbey Pub instead.”
12. After you’ve gotten to know her a little better, make something for her such as dinner or a CD of your favorite music.
This may seem like a lot, but it’s really not. To boil it down, it’s all about thoughtfulness. Thoughtfulness is key. There’s nothing sexier to a woman than having a man who cares about her and isn’t afraid to show it. That means being attentive, considerate, and understanding. Do that and you'll probably see your dating life improve dramatically.