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NYE & 2010

New Years Eve was a pretty good time. Janey and I went out with some of our girlfriends to dinner, drinks, dancing. It was a girls only night and we had such a good time. I made out with some guy at New Years, then Janey and our friend Monique also made out with him after that. We probably had a bit too much champagne at that point but it was all in good fun.

Funny story, Violet emailed me and said she was wasted on New Years at some bar and handed out stickers for my blog (yes, I had some stickers made and the few friends that know stick them to things when they travel) to some random dudes and claimed she wrote my blog. She said she was pretty hammered and cannot remember what she told them, but she remembers making the one pull it up on his Blackberry and read a blog entry about Jayson out loud. She is so funny. So if you ran into “me” this week, so sorry, it was Violet being her drunk and silly self.

I am generally not one that makes resolutions based upon some arbitrary date but that might change this year. 2009 was probably the most challenging year I have had thus far. Not to get too Debbie Downer, but between some personal medical problems (I am fine now!), good friend passing away, my breakup with the ex, losing two grandparents, my company not doing well (I took a pay cut a few months ago), my mom & sister’s car accident and my cousin being diagnosed with a cancerous brain tumor things have been a bit difficult emotionally on my end. I am generally pretty good at dealing with things, but when they all come one after the other, it is almost like you cannot grieve for one without the next one coming.

So, saying that, I do believe 2010 will be a better year for my family, my friends and for me. I am looking forward to new experiences and new opportunities. With that, I have made some changes and one might even call them “resolutions.”

I am starting a new job, which should help with financial issues and provide a better outlet for my creative talents. Like most, I am getting back in shape! I’ve already started running more and am starting a new yoga program. The level of booze will be decreasing, the food is getting better and I am going to start taking time out for my emotional self, too.

And… I should be writing and blogging more!

Now, do not think with all these changes that I will be staying in and not living life. In fact, my plan is to be a little less inhibited (but of course, I am safe!) and just to keep exploring my sexuality. I feel that I’ve been a bit repressed most of my early adult life and it is time to explore what I would like, would not like and just try all sorts of new things and people. I am a sexual person, sexual creature. While I am not going out to “slut it up”, I would like to just be who I am without worrying about the relationship, being with someone, or the ramifications that often are attached to women who do like to explore their sexual desires.

So, my amazing readers, hopefully I can keep you amused and entertained in 2010! Happy New Year!

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Last night I ended up going to a quick dinner with Daniel. He has to go out of town on a business trip and by the time he gets back, I will be with my family for the holiday. We just did a quick dinner and hung out at my apartment afterward for a few. It was during that time at my apartment that I decided to tell him that maybe I was not able to date anyone right now. I explained that maybe I was a bit emotionally unavailable and maybe the timing was off with us right now. That is mostly true, but I did not want to tell him all the reasons why it just was not doing it for me. I am not perfect, in fact I am probably a bit of a mess and maybe the real reason is we really just do not mesh well.

He seemed pretty cool about it. He said he was in no rush, but he was into me, and if I just wanted to be friends right now he could deal with that. I have a feeling that is BS, but hey, the answer made me feel better. We did kiss a little, mostly goodbye, and then I walked him to the front door of my apartment.

It’s funny how in such a short time I went from total excitement about this boy to just not feeling it at all. Maybe the stress I am feeling in life right now, job, cousin having cancer, having to travel soon, is getting to me. Maybe after the holidays I will feel different. Guess only time will tell.

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Another night with Daniel

Friday night Daniel called me on his way home. He calls to tell me he went out for drinks with some friends, he mentioned me and one of his friends knows me. Um, it’s D. Are you kidding? I have mentioned that I lived in the biggest small town ever, and yeah, here is another example of that.

Anyway, I asked if he wanted to stop by and lay on the couch with me as I had gone to happy hour earlier with Jane and I was a bit tipsy and ready for a night of laying around (then hopefully playing.) He said no. Wow, I do not get told no very often. He said the reason was he was seeing me tomorrow night and he did not want me to get sick of him. So, Janey and I ended up just going back out to dinner and late night happy hour.

Saturday rolls around and Daniel heads to my place around 7pm. We planned to get a quick dinner then just stay in, drink some beers and watch a movie. I was exhausted from this week and just wanted some chill time. In addition to that, it’s been a long while since I have been able to stay in on a Saturday night with a boy, and I wanted to see if it felt right with him.

Well, I am kind of on the fence, but more leaning toward the Daniel not cutting it side. Seriously, he is a project. But here is the weird part – I know I am going to eat this boy alive and I do not really want to. He is a nice, sweet, innocent boy that is going to get way too attached and I really do not want to hurt him.

Last night after watching a movie, in which we totally cuddled and were cute and gave kisses, we crawled into bed. We made out a bit, but that was all, and it was me that was stopping it this time. I just did not feel into it. I cannot explain why, but I just was not feeling it. That NEVER happens to me, especially after being five beers deep. I was fine cuddling with him but was not even into making out. OK, that is another thing that weirds me out, I am totally into cuddling with him? Have I been into cuddling recently or something? Because I say I hate it, but when I look back seems like I have been doing it an awful lot.

Also, he kind of pissed me off this morning. I told him every Sunday I do my football brunch. I said I could take him home before or he could come with me. He said he wanted to go to breakfast with me, but not at my spot with my Bears friends. He said he was not ready to meet my friends. Normally that would be fine, but he ended up semi-guilting me, and I stupidly went along with it, into breakfast at a different spot.

I have some thinking to do about this one. It is possible that I just wanted it to work and in reality, it is just not right. Oh, last night as we were talking I realized something very important… he reminds me of a more socially inept, less adorable version of my ex. Yeah, I think my decision should be clear, but knowing me, I’ll probably do the opposite of what I should do.

Also, this is BAD, but I know he is innocent sexually and there is something about his innocence that makes me want to show him a very dirty sexual world. I mean, what is better for the ego than blowing someone’s mind sexually?

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What to do?

On Sunday morning, I drove Daniel to his house. While it is only about three miles from mine, it feels like a different world. After I dropped him off I did my normal Sunday stuff, where I meet my friends for football, brunch and beers.

Daniel went out of town on business for a few days, so I am not surprised that I have not heard from him yet. I have a feeling that he is into me, but one can never be sure about these things. Maybe he is waiting for me to contact him? If I have do not hear from him by Friday, I will think something is up.

A few things I have figured out about Daniel so far are… He wants a serious relationship, he has a horrible sense of fashion, he is best friends with his ex-girlfriend and probably talks about her a bit too much. What I mean by that is like, I do not need to know that she prefers not to wear thongs, etc. Yeah, his awkward dating persona brought that up. But he also is very sweet, very kind and needs someone to bring him out of his shell. I am still debating what to do here because he is the first person I have met that I can stand for more than five minutes, on the other hand he is so much work and is that fair to him and am I ready to deal with that?

Though I must ask myself, why am I wondering when he will call, when he will email? You know what, fuck it; I am going to write him a little email now. I guess I will just say hi, and how was your trip? Hopefully it will progress from there and maybe we can spend some more time together, so I can figure out what to do with him.

On a different note, Jayson is supposedly coming to town next week and he wants to get together. I say supposedly because he was supposed to come last week and for whatever reason had to cancel. He is supposed to land on Monday and he is flying out Tues, but he asked if I wanted to stay with him Monday night. I think if he is actually here I will, but I’ll make my final decision when I have to, but for now I am leaning towards yes.

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W

Janey made me get ready early again tonight to go to another event with free alcohol. Funny, she knows that is my weakness. Of course, we had to leave the house earlier than I’d like, which I loathe. Also, this event was not close to Lincoln Park, but she secured rides for us or I would have never agreed to go.

We walk in, I do not know anyone there and of course I hit the bar. It was just wine and beer, but that was OK with me. This event was for some Sprint 4G thing and basically all we did was drink and socialize with a lot of new people. It was quite fun, I made dirty jokes, I hugged people (yes, I am a hugger when drinking) and we just got a little crazy. Unfortunately, the event was on a Tuesday night last night and today I am paying for all the fun, at work.

But listen to this crazy story! So, Janey and I are sufficiently drunk at this point, this party ends at like 11ish, but we decide we want to go out a bit more. We talk our sober driver into dropping us off at Janey’s fav spot, the W hotel. For a Tuesday night, the bar was packed, maybe a trade show was in town? We are always all dressed up when we go to the W, so I secretly wonder if the bartenders think we are hookers?

We each get a drink and sit at a little couch. We are adjacent to some older men, well dressed, probably here on business. It took them maybe 3 minutes before they moved closer to us and started the small talk. Then as soon as Jane and I finished our drinks, one of the guys made sure we had another round immediately.

I cannot remember either of their names, but I did take some pictures on my cell phone. I am not sure why, but I bet it was because they were so ridiculous that I wanted to remember what happened! So here is the breakdown, as best as my drunken self can remember guy one wanted me, guy two wanted Jane. Both were married and made it quite clear that they were looking for a little hotel action and they had the money to back them up. Oh great, they thought we were hookers.

Guy one put $500 dollars on the table, he wanted to make sure I knew he was serious. I blew it off, laughed and had him order me another drink as I excused myself to the ladies room. I told Janey to come with me. I told Janey what happened and she said her guy did something similar. Then it got a bit weirder. Janey’s guy told her that they were looking for a full on group thing, and yes, he was willing to pay. What the fuck, now it’s confirmed, they think we are hookers.

We walk back to our table, but I stop at the bar. I tell our waitress to remove the first drinks we ordered from our card and put them on the guy’s card. She asked what happened (she kind of knows us by the way) and I said we just got offered money for sex acts, but I made it clear we were not into that but the guy could pick up our two drink tab for being so weird. She agreed.

So then I rejoin the table, I mean, we were getting free drink. It was then just laid out and I never expected this to be said. My guy says to me, here is the deal, I am married, I am from Nebraska I have needs that my wife will not meet. I am listening intently, and I almost know what is coming next. He says, I saw a sex shop not too far away, I want you to go there, purchase a harness and dildo, come back here and fuck me in the ass. You don’t have to get naked, you don’t have to do anything other than that, and I will give you $500. WHAT?

I am over this dude, it just got a bit too weird for me. The funny part is if he left out the money aspect to it, maybe I would have thought about it. I do not want to be a hooker. But I pull Janey into the bathroom again and tell her what’s up and she says, ah, fuck it, just do it. Granted, she was wasted but really?

We go back to the table once more and her guy had already left, claiming he wanted to go to the strip club. Then my guy gave me one last chance to “earn $500 bucks” and I declined. He went upstairs, gave me a room key and said if I changed my mind to just come and visit him.

The best part of this story, as soon as they left us and we were sitting alone… two more married men approached us wanting to take us to the strip club, but we declined, and went home. Sadly, these are becoming typical weeknights at the W Hotel City Center.

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First date with Daniel

Yesterday was a bit crazy, as I packed so much into a very short time.

I went out to brunch with the boy I met on the street, if you do not remember, refresher can be found here. He is super cute, super nice but I am not into him. I cannot pinpoint it other than he just… seemed kind of less than intelligent. He is actually a teacher (in addition to the recording studio stuff), and he seems “book smart” but I think he is lacking in the common sense department.

He did ask to see me again I said we will see but I told him I am pretty busy. That is partially true, as I am going out of town to see my cousin and then going home for Christmas. Plus, I am not really into dating anyone that does not knock my socks off, and brunch boy is definitely not into just fucking. Oh yeah, and I am kind of excited by the thought of Daniel.

After brunch I hopped on the El and went to O’Hare. My friend Marcel has been in Asia for work since January and had a 4 hour layover at O’Hare. It’s been awhile since I have seen him and I wanted to catch up a bit. We were best of friends when we both lived within a block, but have kind of lost touch since we are on opposite sides of the world. It was so nice to just hang and have a beer with him again. He is moving back in June and I am pretty excited for it.

I took the train back to my place, as I had a few hours before I was to meet Daniel. I took another shower, picked out a cute dress, flat ironed my hair, actually wore a bit of makeup and wore cute shoes. I had to drop by the bar downstairs and talk to the manager, as I am helping him with the New Years Eve event they are throwing. As soon as I walked in, the manager and bartender (who are kind of my friends now) made fun of me, as they knew I must be going on a date because I was so dressed up.

After the bar, I got on the El again (just to go one stop) but this time it was to meet Daniel. I was actually pretty nervous, though I have no clue why. I am never usually nervous while dating but maybe I actually want to like this guy. Like I said, I felt something different with him just in our meeting.

I called him as I got off the train and he was just walking to the bar. We met outside, we hugged and instantly I was not nervous anymore. He immediately commented on how nice I looked, which was a bonus. I like compliments.

We sat at a booth in the bar area and started looking at the rotating on tap list. I could tell he was super nervous because at first he was mumbling a bit too much about the beers and not really looking up at me. The waitress came over, we picked our beers and she left us with menus. Same damn thing with the menu, he was so nervous that he wouldn’t really talk to me about anything than the menu. Some girls are really into the shy guy thing, I am not so much, so at this point I am hoping he is able to relax.

We finished our first beer and he was able to relax a bit, thank goodness. We talked a lot, about everything, but the more he spoke the more I realized – he is awkward. He’s only had long term girlfriends, never really dated and he talked about his ex a bit too much. He is an engineer and he totally thinks and acts like one. By that I mean, he seemed very logical and analytical.

We continue to drink and the more drinks I have the more I like him, isn’t that how it always goes? We eat some food, too, which helped sober me up but after 3 German beers I was feeling a bit tipsy. It was about midnight at this point and this particular pub was closing.

We had a decision to make, keep hanging out or call it a night. By this time I was digging him, even with his awkwardness. He is very good looking and seems fun, but just seems very innocent and very shy – which is pretty much the exact opposite of me. So, I give him an option. We could either go home and call it a night or keep hanging out. He has to take a bus to get to where I live and I know there is time constraints, so I offer to let him spend the night if he so chooses. Well, I already knew the answer before he even asked, I mean, come on – what boy chooses NOT to spend the night??

We get a cab and take it back to my neighborhood. We go to this little bar down the street that has shuffleboard and a few other bar games. It was actually pretty fun playing games with him, we joked a bit, poked fun, and he was being pretty cute and doing things like touching my waist as he passed me.

About 2am I was getting pretty tired and said I wanted to go home, he agreed. We walked back to my place and at some point he grabbed my hand. Not my usual thing, but in this case I was liking it. We opened a beer at my apartment and sat on the couch and talked for a few.

I went into my bathroom, washed my face and started getting ready for bed. I also put on just a cute tank top and cotton boy panties, my normal sleeping outfit when with a new boy. Covered up enough, but still pretty sexy. He was in the bathroom while I got changed and I slipped into bed, under the covers. When he came into the room he asked if I was comfortable with him taking his pants off to sleep. My reply – I am not wearing pants, why should you?

As soon as he got into bed, I cuddled up to him. He put his arm around me and kissed my forehead. I started gently kissing his neck (I feel like this is how I start a lot of hooking up?), then his jawline, his chin and finally his lips. It was just a few minutes more before I removed my top. I think he was a bit surprised that it did not take more effort on his part, but I think he was pleasantly surprised. It took him a minute to touch my chest, like he was afraid it was not OK or something.

I should say, our kisses were a bit odd. We made out for quite awhile, but he was not the greatest kisser. It was like he was afraid to be too aggressive or something. He did not really use his tongue, either. Though, his kissing of my neck was really nice.

I decided I was going to have to be the aggressive one, so I rolled over on top of him and hopped on top. I started kissing his neck, biting his ear lobe, and then giving little kisses all the way down his neck to his chest, to his belly. I knew I was not going down on him, but I still liked teasing a bit.

This went on for a bit. I could totally tell that he was very innocent. He seems like the type that when coaxed could be very dirty, but has never had a girl let him do anything he wanted to her. The making out was nice, but just… vanilla.

I did mention to him that I liked to be spanked (do you see a pattern with here?) He said he had never spanked anyone, but he’d be willing to try sometime. That’s a good sign I guess. As we laid there talking a bit more I asked him when the last time he has been tested… the answer… never. What the hell? Then he went on to say he has only been with five women and has never had sex without a condom. He is 30, five women? It turns out he was a late late bloomer and on top of that had a girlfriend who wanted to wait until marriage for sex. Wow.

While he is still a project, the good news is he is willing to learn. The question is, am I willing to take on a project? After talking with him he definitely has some insecurity issues. He is super tall, 6’7, so he said he was made fun of as a child for his gumpy height. Also, I have a feeling he is one of those types that was not very good looking as a kid and then around 22 or so kind of grew into his face. Now he is very cute, but just has no clue.

I want to hang out with him again, hoping he will be a little less nervous next time. I am going to give this one a chance, which means… No sexual activity with him for at least two weeks. I am weird, I know.

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Daniel called me today. He, of course, waited two days. I hate that game, by the way. If you want to call, call. If you do not want to call, then don’t.

He asked me to hang out on Saturday night, which is tomorrow. Now, technically I have plans on Saturday. I am doing brunch in the AM with that boy I met on the street when Violet was in town. Then I am hopping on the EL and heading to O’Hare to catch my friend who has a three hour layover here. He has been in Europe for six months and I would like to spend time with him. After that, I have an event for work at 6:30, but I can probably get out of it by 8pm or so.

I explained all of this to Daniel and he said he would not mind meeting on Saturday after 8pm. I told him let’s plan for 8:30pm – just to be on the safe side. He let me choose the meeting place. Since I knew he was into good beers, I picked this pub with good food and an even better beer selection.

I am pretty excited to hang out with him. Our conversation was nice today, nothing too intense but cute. I have a feeling he is on the shy side. I am very excited for tomorrow, but also a bit scared. Am I ready to date, I mean really date and not just take a boy home with me? Am I going to be able to like someone new?

I really need to remember to stop freaking out and just let things happen. I’ll blog about our date tomorrow ;)

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A new possibility

Tonight I went out with some friends to the restaurant/bar that is in the 1st floor of my building. It’s probably the spot I go to most often, first because of convenience and now because I know all of the bartenders and I cannot remember the last time I paid for drinks.

Thursday nights are usually packed as they have all night happy hour. There was this tall, good looking man in the back corner that I noticed a few times in the night. Because Chicago is really a small town fronting as a large city, of course he knew some of my acquaintances. Well, I ended up telling my friend, Brett, to introduce me, he obliged even though he gave me the obligatory eye roll. Brett knows everyone and I think this is, no joke, the sixth person I’ve asked him to introduce me to?

Anyway, tall guys name is Daniel. He is super cute, very nice and even a bit funny, in a cheesy way. We talked for quite a bit, basically until he had to leave. Before he did we exchanged email addresses and phone numbers. He is from here originally but went to school on the East Coast for a bit and now he is back here, again.

OK, here is the weird thing. You know when you meet someone and you get a gut feeling about them? Maybe it is based on your subconscious or he reminds you of someone else, but I kind of got that with him. I am not sure what it means but, I can tell you right now, I know he will call, I know we will hang out… I know I am going to like him. I have not had this gut reaction since my breakup, so it can be pretty scary.

I am hoping to see him this weekend.

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Last night Janey drug me out to this party for some new technology launch thing. I did not want to go out last night but she convinced me that free drinks + technology geeks = possibly meeting guys with jobs. I know it is due to the economy, but lately Janey and I have been meeting too many jobless guys. I am not really looking for a new boy right now, but she really wanted to go and I was not really doing anything else.

We had to be there at 7pm and sometimes it’s hard for me to get home, get showered, get dressed and be out the door by 7, so I was kind of in a frazzled state of mind. Even though I did not want to go, once I was out I was glad I went. The event was actually pretty fun and I think like 300 people showed up, so there were a lot of new people to meet that were not in our social circle.

Janey knew this guy Jeff just in passing, but they were spending a lot of time talking. He invited us to go out for a few drinks after the event. The place they were going was about 3 blocks from my apartment (and Janey only lives a block from me) so we were definitely in.

I sat across the table from this guy named Tom. He was geeky, for sure, but I tend to like that type. He was very cute, dressed nicely, and as we started talking we realized we had a lot in common. We were at the end of the table, so the group kind of did not notice we were not in the main conversation of the table. He was so nice, so smart, good looking and maybe a few years older than me. We talked about so many random topics from work, geeky things we like, movies, books, travel, etc. It even turned a little flirty. For example, he even grabbed my hand at one point to “look at my ring” and may have held my hand a little longer than necessary.

Like I said, I am not sure if I am ready for real dating, but I knew I wanted to see this boy again.

After about two hours, the bar was closing and we all had to work tomorrow anyway. Everyone kind of went their separate ways. Janey was walked home by one of the guys there, and Tom walked me to my door. When we got there I did the whole, it was so nice talking to you and I was waiting for him to be like we should hang out again, etc.

But instead, he commented on something I had said earlier by throwing in that his wife liked it, too.

What? His wife?

OK, this boy was NOT wearing a wedding ring. It’s fine that he is married, I like new friends, too, but it was obvious there was something going on in the restaurant. We were definitely getting flirty with one another. I am just not sure why it was not brought up earlier. We literally talked about everything under the sun and yet he never mentioned his wife, not once.

Am I at that age where I should just expect that the majority of intelligent and good looking men I meet are either gay or taken? Why would he just not mention the fact that he is married? In our talks about travel especially, he could not have just thrown in a “When my wife and I went to such and such…?”

I was talking to Janey about it and she asked if I thought he was going to entertain hooking up on the side. I honestly do not think he was trying to do that at all, I just think he knew he was flirty and maybe he felt a bit awkward about “leading me on” fully knowing that it would not go anywhere.

Now in the full scheme of things, I do not really care. I mean chances are even if he were single, I would not really pursue it. It is just, sometimes I think I am ready to be in the dating world – I just need to meet someone worth my time.

But to answer the title question of this post… I feel like Tom should have brought up his wife within the first 30 minutes of talking to me, right before it started to get flirty – especially since he was NOT wearing a wedding ring.

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I was unexpectedly hit with a large expense this past week that totaled right around $1,000. When I logged into my savings account to move money to my checking, in order to pay it, I realized – wow, I have gone through about 30% of my savings since my breakup. Now, I know in this shitty economy that I am lucky to have any savings at all. Many of my friends are out of work or literally living paycheck to paycheck.

But this had me wondering, where is my money going, why do I find myself short every month and I am borrowing from my savings? After doing some budgeting (I love Mint.com), I realize I have more expenses now than I did before. Not to mention, last month everyone at my work had to take a 6% paycut.

When my ex and I lived together, he owned the condo and I paid the bills and grocery. My total came to about $700/mo. My current rent is $1250/mo. We also shared a car payment. I did do some savings things like got rid of cable & internet (basic cable comes with my apartment and my work pays for my broadband card), stopped getting mani/pedis every week, slowed down on the shopping and what not. I thought I was being responsible… so, again, where is this money going?

Food & Drinks. Really. Entertainment is my 2nd highest expense, only to my rent. I thought about this for a moment and realized… well, I always eat out. Groceries are made for like families of four, so if I buy something I always feel bad because it goes to waste. If you do buy the smaller size food, the price is so high and there is extra packaging. Going out to eat is easier, less lonely, and perfect for the single girl who wants to mingle with friends. Plus, the ex and I went out maybe twice a week, I go out what seems like every night now. I admit, I go out it to keep my mind busy, to meet new people, to just be out of my apartment, but it is killing my finances!

The other thing about being single (and well, I do this in a relationship, too, but on a much less scale) is you have to keep yourself up! Waxing, Mani/Pedi, Hair products, Hair care, lotions, perfumes, dresses, shoes, makeup, chemical peels, sexy lingerie, condoms – they add up! I am sure guys will tell you, oh this stuff does not matter, but it does. When you go out to a bar, an event, a party, an airplane, this stuff DOES matter because if you look like crap you will not get that second glance, or that first encounter, etc. The world is a shallow, shallow place. I am not saying I do not keep myself up when I am in a relationship, I do (and in fact I strive harder to keep in the best shape physically because I am motivated by looking hot naked) but you have to do many “extras” when you are trying to attract a new man.

Those extras are expensive when you are living by yourself and not sharing expenses. Example, going out 5 nights in a week means 5 dresses, 5 shoes, etc. In a relationship, you need like half the clothing because you tend to go out less. And, oddly enough, because I live in a city and walk everywhere, I am killing my shoes at a very fast rate because I am wearing them more often.

So, maybe I did not make the best choices (perhaps I could have rented a smaller apartment) but I realize that if I keep going this route, I will be broke – and I mean broke – in 6 months, assuming I do not lose my job.

So, anyway, if you wondered why I now have ads on my blog, yes, this is why. I know some people HATE ads, and with good reason, but I need them on here so I can actually keep my blog and my sanity going. I am kind of at that point where every little bit helps.

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