Dating 101: Can Women ask Men Out?

I wrote a man on this week.  His profile was beautifully written, lacked the typical stench of online dating crap, and he was just the right amount of sarcastic and funny. He is handsome, smart, Jewish, and entertaining.  He wrote back and we ended up speaking on the phone.  It was an easy and comfortable conversation. We had a lot in common and I was surprised by how “normal” he was.  It was a very nice exchange and I liked him a lot.

We spoke again later in the day and it was great.  He is very easy to talk to and I laughed easily and often.  I wonder if it is because he is not from Los Angeles, and has a more Canadian vibe, being from upstate New York.  He lacks pretention and smugness, which I found to be really attractive.  He is adorable and I have a little bit of a crush on him.  After two phone calls however, we spoke of plans to meet, but he did not ask me out.

Dating online is a numbers game. I get written to a lot but there are very few men I actually go out with. When you come across someone that you would actually go on a date with, and they don’t ask, it is frustrating.  It is also confusing.  If he liked me would he not ask me out?  Is he just being nice? Am I in the friend zone and therefore not getting a date?  The most secure person can be made to feel out of control and desperate.

Not desperate for a date, but desperate for clarification. I have old fashioned views in terms of men and women and their roles, but at the same time I am bold and fearless in how I approach dating, so the question becomes: should a woman ask a man out or wait for him to ask her?  Instead of worrying about why a man does not ask you out, why not just ask him out yourself? What is the worse thing that can happen? He says no?

I spoke to this man a couple more times and again, great.  After 4 phone calls, and talk of getting together, I decided I was simply going to ask him out. I panicked for a minute and asked my Twitter and Facebook followers if it was appropriate for a woman to ask a man out. The responses were interesting, but not very helpful.  I heard from men and women, and it was a split decision of both good and bad for me to ask him out.  Oy vey.

The biggest problem I have with dating is me.  I over think everything and assume there is some big thing going on that I need to figure out.  The fact is that dating is very simple.  You meet someone, decide if they are worth pursuing, move forward if you do, and move on if you don’t.  People say it is the heart that confuses things, but before the heart is even involved, it is the brain that screws us up. Dating requires us to stop thinking.

So I had plans with a friend for dinner this week and she cancelled because of work.  I was having a particularly fabulous hair day and didn’t want to waste it, so I decided to be brave, stop thinking about it, and ask him out.  I asked, and he said yes.  He hadn’t asked because he is working on a project for work and unavailable until next week.  Why didn’t I think the reason he hadn’t asked me out was because he is a busy professional and dad?

We made plans to meet next week and I am looking forward to it.  I was happy I asked, he was gracious and flattered that I asked, and life goes on. I think we will go out next week, and the thing is that if we don’t, it will still be okay.  I am dating and it sucks, but it is better if I allow myself to be me and me has no problem asking a man out.  The truth is that a man who does not like  a woman to ask him out is probably not the man for me.

If I am able to decide where to go on a date, whether or not to kiss a man, make out with a man, and sleep with a man, then why am I so hesitant to ask out a man?  Instead of thinking I am brave, I need to remember I am brave.. I asked a man out and the world didn’t stop turning.  Go figure. The key to finding love is to be yourself, and I ask men out, so we’ll see if my bravery pays off and he really liked it.  Until then, I am keeping the faith.