A Dating Question: When is it Okay to Have a Conversation About Sex?

I met an interesting man online this weekend.  He was funny, educated, Jewish, handsome and charming.  He was married for 25 years and is now divorced.  We emailed, and then spoke on the phone.  It was good, until we got to the topic of sex, and I’m not exactly sure how we even got there.

We should talk about sex. We are older, experienced, and aware of its importance.  For some it’s not a big deal, and for others it’s the key to a successful relationship.  I think it’s important, and I want to be with someone who is on the same page as me in terms of its value.

I’m just not sure I want to talk about it before I’ve met the person.  It was a good talk and I learned a lot about him.  He was respectful while still clear on what he is looking for.  I admired him for jumping right in, and at the same time was turned off.  I felt intimidated by the conversation, not sure how to participate.

It could be, God forbid, that I am simply not as evolved as I thought I was. I feel self-conscious, which is ridiculous because we have not met. I know details about him, which I find odd.  I was looking forward to meeting him, but now I’m not sure.  The realization that I am not cool, sucks.

I’m not a prude, but it turns out I’m conservative in terms of what I am willing to talk about.  You wouldn’t know it from this blog, but I am a little shy one on one. There is a time and a place to discuss everything and I think a talk about sex should not happen before you’ve met someone.

What’s the harm in meeting first, seeing if there is a connection, and then worrying about the sex? I spoke with the gentleman again this evening and we discussed that I was writing this blog. He was flattered that I was intimidated, which I found both charming and unattractive.

He might be a pervert, or it could also be that he is just a grown up who is comfortable in his own skin.  He is 14 years older than me so it could be an age thing.  At almost 60, he is perhaps just better able to articulate his opinions.  Not to be shocking, but to simply be honest.

I feel a little unsettled.  I want to be free and open, and at the same time I want to be respected, and this conversation blurred the line for me.  I like him and tonight we laughed and talked about a lot of things, but I kept thinking he would jump to sex at any minute and it was weird.

I could be over analyzing the whole thing, and he’s probably not thinking about it all.  I could be trying to sabotage him before I even meet him, which could mean that I like him.  Our conversation made me wonder, when is it okay to talk about sex with someone you are dating?

More importantly, is it okay to discuss sex with someone you have never met in person?  Furthermore, can you have sex without a relationship, or a relationship without sex?  Does sex naturally become important to a couple, or do we make it important based on our desire?

Sex is important, but not something to talk about before meeting.  If you meet, and want to spend time together, it’s still not something to talk about. I sound like an old lady, but at the end of the day, that’s what comfortable.  I’m fine with what I said and didn’t say, but he crossed a line.

It was not a lewd or graphic conversation.  It was simply in poor taste.  I can be tough, and if I get in a situation that is uncomfortable for me, I get myself out of that situation.  I’m good at keeping myself safe and that is the issue.  Will I feel safe if I meet with him in person?

I’m not sure I want to meet him anymore, which is silly.  Nothing he said was threatening, it was just too much, too soon.  I’m an independent woman, but still old fashioned.  He was not offensive, but I was a little offended.  Does that make sense to anyone other than me?

I’m on the fence with this one.  I need to stop thinking about it, which we know I won’t be able to do.  Sex needs to be talked about at the right time. By right time, of course I mean when I decide it’s cool.  Will I meet this man in person?  I don’t know, but I’m keeping the faith.

** Tonight I will be a guest on the “Keeping It Real” Radio Show with Robert Flutie and Aaron McCargo Jr. at 4:00 PST – 7:00 EST.  It will be interesting to get men’s perspectives on this blog. Robert and I met in classic LA fashion and will share that story.  Aaron and Robert are a fun pair, so it promies to be a lively conversation.  You can listen live online at Radio Show or on the radio at WTAN-AM 1340 / WDCF-AM 1350 TAMPA BAY.  I am looking forward to it and hope you can join.