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Dating for the inexperienced


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I am 28, never been a relationship and have yet to do anything more then kiss a woman in terms of my sexual experiences. It's not because I am ugly, awkward or unsuccessful, my life is quite the opposite and my struggles seem to be mainly in the dating world. Again, I don't get awkward on dates or anything but I seem to lack the experience or skill to keep things going. I always think about "what the he!! am I going to say" or "oh boy it's the second date I HAVE to kiss her" or "jeese what am I going to do when it comes time to get down to business sexually, I am not even going to have any clue what to do or where to even start". Now a lot of this is me psyching myself out and I am trying to figure out ways to relax and be myself.


I just recently went on a date with someone I met online. We met for drinks and when she showed up I couldn't believe my eyes. She was gorgeous and better looking in person, quite different then most of my first online dates I've had in the past. We talked for almost 3 hours, laughed and shared quite a bit and did however end up the last 20 mins or so with awkward smiles at each other, looking away at the band or pictures on the wall. I don't necessarily take this as a bad sign as I feel this is normal. We called it a night and she did say she really wanted to see me again and gave me a kiss on the cheek. Later that night we traded texts and I received the best compliment I've ever had after a date. All it said was "best date in a long time I couldn't believe my eyes and it put a giant smile ear to ear. So, this is the reason I am reaching out for help.


Now I do like her and would love to get to know her more and obviously she wants to see me again as well. We've traded a few texts here and there through out the week and am actually taking her to a comedy club on Friday night. I really could use some tips about how to stay cool and not go over board with being nice or tips what I should avoid to ensure there's a third date. Her and I talked about our love for cooking so I am planning a surprise third date, assuming there will be one, for a cooking class. I just want to make sure that it's not too much to plan such an outing for a third date. And as stated before could use some tips about how I can go about being psychically intimate with her without looking like a complete moron.

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First of all, relax and remember to breathe. Random thoughts:


It sounds like you're successful in other areas of your life, so I'd guess you must have to interact with people, right? So I'm guessing maybe you're just not good at small talk? I've been that way in my life, and there are many good books on the subject. The most universal salvation I've found is to ask someone about themselves and be an active listener. Not having to worry about what to say next takes a lot of the self imposed pressure off of the situation, and your best self can come through.


It sounds like she likes you, so whatever you did on the first date, simply continue it. A comedy club sounds like a great venue. There will be lengths of non-talking time when you're watching the show, and the show will give you lots to talk about when it's over. You're sharing an experience together, and that's very bonding. There's no magic light show requirement on your part.


As far as sex, I'd worry about getting through the first kiss, don't you think? And the thing is, don't worry about it. At the end of the second date, find the right time and lean in to kiss her. Don't worry, she'll know what's going on and if she's into you, you're going to have to screw up pretty bad to change her opinion. If she's they type that wants to make you work for it, then she's probably not the girl for you. But from what you've said about her, that she said she wanted to see you again and you were the best date she's had in a long time, she doesn't sound like a game player. So relax on this one - you're not there to "take" something - you don't have to be smooth and suave and debonaire. She's either a willing participant, or she isn't. So far, it sounds like she is.


Don't be afraid of silence. I've always found it a test of a relationship when you can be with someone and still be yourself. That's when you have a winner. Do you want to be with someone who you feel like you always have to be "on" when you're with them...don't you see how that would get tiresome? It doesn't work long term. So if there's silence, don't automatically assume it's awkward and you need to entertain. Relax into it, and she'll do the same. It sounds like you're golden.

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Lol, that is awesome, dude! Congratulations!


Don't compliment her too much, say you are nervous if you are really getting sweaty palms, and just smile a lot - be confident about the great guy that you are, and treat her with respect.


You are super cool! Just stay calm... When the time is right, you will kiss her, and it will be dope as heck.

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