Tag Archives: lesbian community

Having It Both Ways: First Date

Having It Both Ways: First Date

Read more about the Having It Both Ways series here.

I’m pretty sure I haven’t been on a first date with someone like… ever.  Most people I get to know they become friends and then it turns into something else.  Rarely have I had the balls to say to someone – wow, you’re really interesting, I would like to have goat cheese and oysters with you on a Friday evening.  Enter Mixology, stage left.

So tonight was my first date with who we will lovingly refer to as “The Librarian.”  Not because she looks all old and school marm-ish.  Think more… Music Man.  She was truly delightful and had the most amazing eyes.  There were MANY awkward pauses where …. I didn’t know what to say… and I guess neither did she.  It was weird.  Then we discovered we were both English majors.  Then started talking about Shakespeare and an improve Shakespeare troupe in Chicago called – I think IO, I’ll ask her.  Then find out she likes Aaron Sorkin and The Gilmore Girls and BUFFY and Joss Wedon.  The conversation flowed as nicely as the wine.  She’s also really into new media and coms and is a fan of the twitters.  So this is pretty cool.  Lots of fun geek conversation could erupt from that.

Stupid things I did… told her about how easy it was for Rico and me to get girls in college to send me naked photos of themselves by using the phrase “Don’t worry… I’m a professional.”  I talked about my dead kitty which was sad.  She has a kitty – this is good.  I talked about how I tweeted before I arrived about how it was a bad idea to live tweet the date.  She gets total props for telling me she’s a twitter addict and I can check if it I want to.  Big smiles.

End of the night she didn’t ask me for my info I asked for hers.  Is that a good or bad thing?

This was good.  I had fun, what a lovely person for my first time.  Food was good – I ate too much.  I got wine, she did too – I hope that’s normal….  What else?  Any questions?

Having It Both Ways: Might be the craziest thing I’ll ever do

Having It Both Ways: Might be the craziest thing I’ll ever do

Hear more about the Having It Both Ways project here

UPDATE:  And so my mother is freaking out now… because of the money…

So I finally filled out my taxes.  This is a good thing because I can now spend that money on the dating service I just paid WAY too much for.  That’s right… Mixology is now going to find me a date.  My mother will be displeased by this because I think she secretly wants me to find a nice man to settle down with – but frankly, I don’t have a hard time meeting men.  If you live in Washington you notice them everywhere… there was the one who stalked me for a while, the one I met on the metro, the married one, friends of friends.  Men are a dime a dozen.  Women are more difficult.  Professional women who are well rounded, socially conscious, and don’t want children… I’ve learned are more complicated.

That’s where Megan and Kim at Mixology come in.  Apparently the fact that I’m open to dating a variety of different races between the ages of 27 and 45 means that I’m going to get a lot of dates.  This apparently makes me versatile.  I wanted to say “Yeah… you have NO idea…”  They shoot for 6 a month – I could end up with as many as 12.  The issue is being available and open and quick to report back on how things went, what you liked about her, and what you didn’t like about her.   You decide if you want to see her again.  I’ll always give her my card at the end of the date just because it’s important to make contacts and friends even if you don’t want to spend the rest of your life with the woman. . . .

So, here’s the other part of this coin: how do I break it to these lesbians that I’m also into the dudes?  Suddenly, I’m coming out all over again.  I guess being who you are is key and if I can get 12 women a month moved through then perhaps I’ll be in a position to be choosy or more will choose me.

The sticking point was payment.  When I talked to them on the phone it was $2500 up front lump sum – they are letting me pay it out.  I just can’t believe I’m paying money for this.  It better get me somewhere and if it isn’t love, at least get some views on the blog post.  At the very least I’ll be reporting back if the service works, how it works, if its worth it.  It makes you initial that you’ll do due diligence on STD tests before you sleep with someone.  That you’ll represent them well at restaurants and not be an asshole to the wait staff (sad they have to even SAY this).  You can pause your account at any time for up to 6 months.  So lets say you meet someone you want to focus on – pause it.  Once you start sleeping together – you’re required to pause your account.

Here’s the first page of the contract below.  I’ll post the other pages when she scans it and sends it to me.  HERE WE GO!

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Having It Both Ways: Lesbian Online Dating

Having It Both Ways: Lesbian Online Dating

The HelpIf you haven’t read the introduction to Having It Both Ways please feel free to read more about the project.

I have a lesbian friend who just moved to Chicago and has been trying to meet new friends and date women in a city where she knows no one.  We both created our “How About We” profiles together a few weekends ago me for DC her for Chicago.  She’d never tried online dating sites telling me “a couple people I know had met some total fucking psychos and also I think I still saw online dating through a 1997 lens.  It’s weird and seemed like not as “pure” as meeting someone some other way.  Then there was just the total crippling fear of being rejected in yet ANOTHER medium.”

So she’s been working on another profile on OKCupid because she says we’ve seemed to be early adopters to “How About We” which has a lower number of users.

The key to online dating sites is basically selling yourself.  Think of it like a virtual personals ad.  But you can’t extrapolate too much, otherwise you’ll end up with some person who figures out who you really are and has no interest in seeing you again.  In my very limited experience and my friend’s – be honest about who you are.  Always… be honest and think positively about your positives.

“I feel like I’ve tried to be pretty honest about myself and who I am” she told me via GoogleChat “But then I feel like that is prolly why no one has messaged me.  Like if I had a different “persona” I would have better luck.  In general I feel like there are certain personas that go over really well with lesbians and I am not it.”

I told her that lesbians work in cycles.  Right now there are a dozen women out there that are breaking up with partners or girlfriends.  Finding the perfect person isn’t like turning on the channel guide and finding something to watch for the evening.  It took me 3 years before I really fell for Dude #3 and clearly that didn’t go well, so it’s all about being brave and trying new things and giving it time.  And for the love of God – know that you’re perfect the way you are, own your own awesomeness!

Read more about insane dating options for lesbians or straights (but neglects bisexuals).