New Year is starting off right!

December was a crazy month for me! Hell, even November was, but that was because I took a 10 day staycation to Indianapolis. Super Fun! But then I was unexpectedly home for 2 weeks in Indiana with family.

Since this took a toll on my social life, I feel like I have lost time to make up for. Good thing I have 3 dates scheduled this week! Can’t wait to blog about them later this week!

In the meantime I am semi-stressing about what to wear as the weather we are having in Chicago is crazy! Normally, I would be in skinny jeans and a cute top, but with all the snow all I can think about wearing is sweatpants and Uggs. Along with no judgement from my date.

This made me think I am sure others in such wintery areas have the same dilemma. I always feel my cutest in some high heels, but that will not be happening this week. Listed below are a few outfits I would totally wear for a first date.

dressy casual 2 I love grey! I love that this olive top is a bit flirty yet the sweater brings it in the make it more cozy. Not a huge fan of the style of boot it is, but pairing it with a similar grey boot or even black I think would totally work. Of course completing the outfit with a cute scarf and earrings would be my choice.

dressy casual 4 Love the loafers! I also just love the simplicity of this outfit. Cute jeans, cute sweater- done and done.

dressy casual 3Love the red! I am a true believer that red is a power color. I think it just makes you feel more confident and after all we all probably need that on a first date! I am digging the cardigan as well, but I must warn you, be careful of flowy open cardigans. They can make you look frumpy if they are just too open. I normally by mine a size smaller to get the appropriate effect.

dressy casualThis is totally my winter style. I love a good simple tank or tee-shirt to go under a cardigan or sweater. I think a great bold necklace always make any outfit look dressier than what it is. Loving these tall boots, but they could still be a challenge to walk in when it is icy and snowy.

blazer Lastly, I feel like  you can never go wrong with a blazer. I am also a HUGE fan of color blocking, when it done correctly. The only changes I would make for this outfit would be to wear a more neutral shoe (black or nude) and bring a neutral handbag. Too much color blocking can make you, in my opinion, look like you are either 12 or a drag queen. Neither are flattering when  you are trying to make a decent impression on a first date.

Enjoy my style, and if you have any suggestion on what you would wear on a first date, I would love to hear them!


Date with the Pyschic

Happy New Year Readers!

As you can imagine the holidays and a family emergency has set me back a little bit with blogging and dating. So I thought this would be a perfect time to share with you about the date I had with a psychic!


Psychics- god, I love them. I would not call myself a religious person by any means but I am definitely spiritual.

Last year, my good friend came to visit me for a girls weekend and we decided to do something really dumb and random- get our palms read.

We went to this psychic that was right around the corner from my apartment. The psychics name was Janet. She was amazing. Janet, if you are reading this, please send me a message!

She touched on things that really only my close friends and family would know. Now, just so you all know, I was skeptical about what she had to say. She did start off by telling me about my personality, which she nailed, but come on-she is probably just reading my body language.

But then she got to the real stuff. She hit it on the head about my ex and how I was still suffering from the break up. True. She told me that I don’t trust easily. True. She also touched on facts about my childhood- all which were true as well. There were a few things that didn’t make sense, like telling me that I have a little girl spirit with me. Not sure I will ever know the truth about that one.

One interesting this she did tell me was that I would meet my soul mate within a year and half. The one year mark hit in October 2013. Not sure if I will really meet my soul mate within this time frame as I am not dating anyone seriously. But I still have faith, as when she told me I would me getting a new type of job and then moving all within 5.5 months, that did happen.

Looking back I guess I should partially thank Janet for a wonderful reading because it made me want to better myself. Break down the trust wall that I have put up and really try to find my soul mate. I started this blog to help me branch outside of my comfort zone and just go for it! After all they do say that you need to kiss a lot of frogs before you find your prince.never give up

Have you missed me? It’s been a while…

So it has been a little over a month since my last blog post. One, the dating life has been semi slow, but my life has been crazy!

In November, I planned a staycation with my besties down in Indianapolis. I was there for 10 days drinking, laughing, shoving my face with all sorts of fast food and of course causing havoc on the town.

In my attempts to keep my Tindering skills strong, I went ahead and came up with a very creative tag line- “In Indy for 10 days. Who’s down to clown?” MAN! you wouldn’t believe the amount of messages I got for one night stands. Talk about an ego boost! For the record, I did not have a one night stand or meet up with any of these dudes, but it sure was nice playing with their heads. So of you might be asking why didn’t I meet up with any of these dudes, but this was a girls trip. And I am loyal to my ladies first! If I was some place warm we would only be flirting as well.

After my 10 day drinking binge, I then had to prep myself for Thanksgiving with my family. Which means I knew for 3 days I would be asked the same question in 20 different ways as if they thought I wouldn’t catch the similarity…”So are you dating anyone?” Ugh. Kill me.

Don’t you think if I was dating someone SERIOUSLY, I would be acting like this:OMG Elf

Instead, this is my reaction. As you can see the reactions are almost identical so it is very clear as you why my family is confused as to if I am dating someone.


Yes, I am dating. And not just someone but multiple people. But, I can’t say that because if I am honest, I now look like a slut to my family. Family never seems to understand that dating doesn’t mean I am sleeping around. It means I am trying to score a free dinner people!

This month has been full of year-end work parties and get togethers. I have managed to squeeze in a coffee date but I just felt so so about it. Nothing big to report as it was just a coffee date.

Umm, hello? Didn’t you just tell me you had a girlfriend?

isabelle...mixed signals

Ah, my date with The Consultant is a good one. But first, you should know the background on how we met.

I was meeting one of my girlfriends and her husband downtown for Oktoberfest. She invited me because she didn’t want to be the third wheel during “bro time”as her husband was meeting one of their guy friends. Little did either one of us know is that The Consultant and I would really hit it off!

He was attractive, confident, funny, mature- holy hell, did I just meet the total package? We shortly moved closer and closer to one another having a great conversation and exchanging numbers. Being a consultant and all, The Consultant was traveling back and forth between Chicago, San Fran, Dallas and Hawaii. Must be nice, huh?

This led us to texting most of the time, and holy hell, it SUCKED! We had the worst text chemistry ever. But every time he was in town, we seemed to be having double dates with our mutual friends and still really hitting it off. And I know it was just not in my head because even my girlfriend would comment how much he seemed to like me. We even both ended up going stag to their wedding and basically became each others date.

Over the next few months, I started picking up that he might be dating some one else- like seriously. I wasn’t hurt by this after all we were not dating but I was confused. Was he just afraid of committing because even though he was talking to someone else, he was inviting me to the cities he was visiting/working- and for free. Probably should have tried a bit harder to take him up on the Hawaii offer.

We both had a few busy months ahead of us, but after about a month or so of him traveling he was finally back in Chicago, and finally asked me out on a real date! Or so I thought he did…

We ended up meeting at Webster Wine Bar, ordered food and had great wine flights along with great conversation per usual when we were face to face. Then the awkward part came- he told me he had a girlfriend! WTF?? Now, it didn’t just end there- he went on to complain about what he didn’t like about her. Maybe he felt bad because he did like me- I don’t know, but I was stumped.

I finished my last flight as soon as I could, made the best conversation I could because after all we have mutual friends, I will see him again. And then it got more weird- he asked what I was doing for the weekend. thank god, I was heading out-of-town for a friend’s birthday, and when I told him that he told me maybe he would come down a few days later to hang out with me. Umm, hello? Didn’t you just tell me you had a girlfriend?

slut, wine and dine

Tales of Tindering

With my experiment of not putting all of my eggs into one basket and Tinder (the dude) pissing me off, I decided to give my number to a few other Tinder prospects.


Story 1:
Because he is weird, and I know I will not ever be meeting up with him, we will call him Jake- his real name. The guy doesn’t deserve a nickname, honestly. So our Tinder conversation was normal- how are you? what do you do for a living? blah blah blah. He went in for the kill right away- let’s exchange numbers and meet for drinks. Ok, sure why not, I thought.

Well once we exchanged numbers, he proceeded to text me anywhere from 4:30am to 6am- all times when he woke up. Seriously, Jake? You may work in the banking industry but pretty sure I informed you that I have the joy of actually working banker hours. I sleep in until 7:30am or 8am. Strike 1.

He then asked me how tall I was…why? I mean I understand we all have our thing, our own ideas, wants, and expectations out of the perfect mate. I like tall dudes because some nights I wear 5 inch heels- I get it, but I don’t ask the dude before we meet how tall he is. Weird. This day I also got a selfie of him in his office.

The next night he tells me he is writing a book, I ask about what but turns out it is top-secret and he can’t tell me. He then asks me for my last name. Uh, not so soon buddy. Stalk me on Facebook like a normal person, I know I am not that hard to find. Strike 2 because I am just annoyed at this point.

There is no reason to give Jake a strike 3 because I just do not like him. He starting hinting like he was going on dates- like I was going to be jealous. Yeah, no. I slowly just stopped responding to him, ok that’s a lie…I just stopped completely.

Story 2:
I started messaging this dude last week. We will call him Naughty Pic Dude. So Naughty Pic seemed very normal, as they all do, during our first few days of Tindering. He lives closer to me than the other Tinders, so score 1 for me! I am thinking we probably like/go to the same bars, like the same places to eat and it’s always a plus when I can take a train to your house than a cab.

Shortly into our normal conversation, Naughty Pic asked me for my number. Yay! Maybe he will ask me out for drinks and we will have a good time. Even if it doesn’t go anywhere, at least he could be fun and I wouldn’t be putting all of my eggs in one basket.

Wrong-o, he turned into the weird guy that texted me right away and asked if I was down for a “naughty picture”. Really? I mean I get it, sexting can be fun… but we haven’t even met in person. Do you think your “naughty picture” is going to make me want to meet you more or sleep with you sooner. Confusing. He also was a selfie picture- the normal kind- taking kind of dude. I like pictures… and sending dumb ones of what I am doing, but shouldn’t we ease our way into them?

Maybe Tinder (the dude) isn’t really pissing me off too much anymore…

Date with the Virgin…sort of

virgin ecards

After going through a not so pretty break up, my friends where there to get me right back in the game of dating! Love them.

Well, one of my best friends here in the city had a friend that just moved here from the east coast. After thinking about it, I had already met him at her house-warming party about 6 months back. I most certainly thought he was very attractive but didn’t really give him much thought as after all when I did meet him, I was dating the ex.

In efforts to get us both out on a first date, my friend would have us over for dinner at their apartment leaving us to share a cab home since we both lived in Lakeview. She and her husband would get us together for drinks at the bar, and leave us there to chit-chat.

The Virgin and I always had a blast together. We got drunk together, we danced together, we shared stories, met each others friends- but never went on a real date, nor did he ever try to make out with me. This routine of our lasted for about a year. Was he a Virgin???

Of course, after a few months of this routine, I knew it was not going to be going anywhere. He confirmed this one night when we were out and he said let me buy you a beer and it was a PBR (I mean, really? You couldn’t spring for the Miller Lite?). Then he confirmed it again when he said we can’t date because we have mutual friends. Got it, moving on.

The Virgin ended up moving away and I went to his going away party, with my friends that introduced us, and in true form and maybe one last hurrah, they left to go home and I went to party with The Virgin at a 4am bar. Being late and drunk, I invited my ex to meet us out at this bar as well- I mean after all, The Virgin has made it very clear that  we are just friends, I didn’t think this was a problem. Until he told me that he would just stay at the front of the bar with his friends because he didn’t want to be around my ex. And the kicker…he then asked me what we were because he thought we came to the bar “together”.

He was moving the next day and I am pretty sure the look on my face was something like this:


Play Ball!

3 strikes

I am a three strikes and you are out type of person, and while I was in the shower this morning, it made me realize- is dating like baseball?

Maybe this is because Tinder is a baseball fan and he has been on my mind more than ever lately, but this really might be true! You get 3 balls- or maybe it’s 4 balls- and then are allowed to walk to first base, these are dating gimmes, and then the big strikes- 3 and you are out.

As much as I was thinking Tinder had used his 3 strikes, he has not… he has just used his 3 balls (that sounds weird… and dirty, but you get my point!):

  • First ball- broke our first date due to his sister having a baby. Legit!
  • Second ball- could not meet me out for the Wicker Park Food Crawl due to a car accident. Legit!
  • Third ball- broke our rescheduled 1st date because he was hung over. Legit, but less legit than the first two reasons.  DISCLAIMER: Thank you for not wanting me to watch dry heave. In my moment of being annoyed, I did not state this, but it is much apprecaited.
  • If there are 4 balls, make up your own forth annoying thing that would hinder the first date.

After these 3 things, my first reaction would be to write him off- completely. Delete his text messages, delete his phone number etc. You get the idea. But, that’s just the bitch I pretend to be. Deep down, I have so much faith in Tinder. I am normally a pretty good judge of character (Yes, that is a pat on my own back and I like it!), and this one seems like a keeper- go figure I start a dating blog and maybe meet someone I could potential start a relationship with- story of my life.

I didn’t want to let Tinder walk to first base- Screw that, I am annoyed!!!! However, writing people off way too soon and way too late is a flaw of mine and truthfully, part of the reason I started this blog was to change that. I decided to let Tinder know I was annoyed and he was very sweet to offer to reschedule for the next day, but I was not up to committing- after all you can’t change over night! I asked him to get a hold of me the next day and we will see how we felt and what our plans were. I just felt that every time we have made plans, they get squashed some way, some how. I couldn’t handle being let down again as by this point I am pumped to hang out with Tinder.

I did not hear from him until 9pm the next night. It was a text that just said “Hello.” How the hell do you want me to respond to that one, TInder? Sure, you screwed up and know this, and probably are saying this with your tail between your legs, but good God, just a hello?

Tinder calls me around 10pm. I won’t lie, I was not sure if I wanted to answer his call. But because I only talk a big game, I did. Tinder is the type of guy that I really don’t think will lie or if he does, wants to- not like any of us want to lie, but point being is he is not being a selfish dick. He wanted to be honest with me and showed up at my house- with his over night bag packed. How could I say no to this? I am such a softy at heart, and secretly love to snuggle. DISCLAIMER: It’s safe to say strike 1 is wearing away at this point…and in my head this is playing out like John Cusack in Say Anything…..

John Cusack say anything

Tinder and I spoke about what was going on with him- ugh, the dreaded ex-girlfriend. DAMN IT!!!! How can I compete with that? I have been in his position before. Remember Tornado? He showed up at my door step, in a blizzard, telling me how much he missed me and the grass wasn’t greener on the other side. With Tornado, I thought ok, not a problem, you just needed to miss me and everything will be better and we can pick up where we left off. Wrong, we still broke up for a reason- a big reason that couldn’t be fixed.

Don’t get me wrong, if Tinder still has ex-girlfriend problems, I need him to figure those out before we can start anything. What throws me for a loop-hole is I did not expect to feel this way about Tinder- AT ALL. I am such a tease and have such a huge wall up all the time that recently, I don’t let any male in. But, Holy Shit! Did Tinder just knock down the wall a little bit without me realizing it???

<instert your own explicit here- mine is FUCK!>

cursing symbol

Tinder and I have talked probably every day for the last month and a half and not talking to him today almost left this void in my day. Once meeting Tinder, I automatically felt comfortable around him. Sure, you get the weird butterflies just because it is new, but there is nothing normal about how we have been dating for the past month. He has met all my friends and we have spent the night at each others houses, and we still have yet to have our first real date. Needless to say, he doesn’t make me feel like I need to pretend about who I am or cover anything up because “it is the beginning stages.” I like that Tinder can just go with the flow because after all there is nothing normal about my life.

Today I realized this about Tinder:

  • I  really like this kid! Not that I didn’t before, but can now see that it just isn’t someone is “paying attention to me and I like that” type of feeling. Ya know?
  • This kid gets my jokes. And throws me for a loop with his. God, I love good banter.
  • I like that I can be honest with him. He doesn’t make me want to yell or pack his shit up and throw it down the hallway. He listened to me when I stated I was annoyed and instantly tried to make it better.
  • We didn’t talk today, and all day I kept checking my phone for just one text message. Do I miss him already or do I just miss having someone to text with?
  • Oh, Shit! I really like this kid!

I think Tinder feels the same way or slightly the same way based on the things he has said to me. So Tinder, if you are reading this, I am not ready to write you off (like I tried to convince myself I was on Sunday) and as you stated, I really hope we have a better string of luck. You also haven’t gone through your strikes yet so why quit now? Oh God, did I just make myself look desperate…. well, whatever, it wouldn’t be the first time nor will it be the last.