Brews, Baseball, and Boy

After the boy became handsome, I wanted to talk to him all the time. He was traveling yet again and I offered to pick him up from the airport. My friends were all too curious as to why I was flying a booty call into town because NO ONE gets picked up from the airport. Except my mom. I had to clarify that this guy I was dating was coming back into town and that I was picking him up.
Again, the disbelief. You must really like this guy, they said.

In the four days he was gone, I missed him a ton. I let him interrupt my sleep with drunk dials hoping he'd profess his love. When I picked him up, I brought an arsenal of snacks and he brought me the most amazing bottle of pinot from Oregon. Alright, this kid knows the way to my heart. We had a real thai dinner (I took him to the right part of Chicago for that) and enjoyed each others company alcohol-free. We then went back to my house and continued talking well past midnight.

The next day a friend hosted a BBQ and I extended the invite; he'd be meeting two of my close friends. Fortunately, he took to backyard games like a frat boy takes to beer pong. So much so that this semi-athletic guy kept kicking my ass in every game. No, I'm not competitive. He fit in seamlessly and entertained conversations with guests. We shared some brews while he continued to dominate lawn games and I was secretly proud that he was a ringer. Ha- the little things.

The next day (three days in a row, people), I invited him to a Cubs game with the same friends. First off, he was more than happy to attend a baseball game with three women. That in itself is impressive. On top of that, he insisted on buying all the beers for me and my girlfriends. While on a beer run, I asked my friends for their honest opinion to which they responded with a resounding, "we love him." Yes, you can win over my friends with beer.  That plus a gregarious personality and the ability to have fun in any situation. In spite of the cubbies performance, I was having the best time ever. He joked that he liked me better after a beer or two because I became sweeter person. Ha- he probably has a point. We used a friend's connection to get on the field after the game and I think I scored him some bragging rights. I was even more than happy to take photos with him! I'd be hard-pressed to find a picture with any of the guys I've dated in the last 5 years; no one made it near that point.

It was pretty clear that I didn't want to go on a date with anyone else and later that evening, we mutually deleted our dating apps. I can feel myself getting sentimental and losing my edge. While I want to continue this blog, it might get all sappy. I'd love to hear from you. Should I keep writing? And yes, he knows about it.

He Won a Bet and I Pay My Debts

You'd think that I'd be sure of this after that amount of facetime, but I wasn't convinced. I owed him a dinner date in the three days before he traveled and part of me wanted to schedule a first date. Another part of me suggested getting dinner the DAY AFTER date two. Back-to-back dates? I can't recognize myself.

When we met for an early dinner, we did not hold hands. We did, however, agree to not have any drinks today and immediately ordered wine when we were sat. Just a glass. He proved to be a formidable dining companion. Wine aside, he was also great at letting me order while providing some suggestions. You have no idea what kind of dining idiots I've seen out there. He thoroughly entertained me with story after story and practically got me to choke on my wine laughing. Twice. I might have had some feels creeping up.

On the walk back from the restaurant, he didn't hold my hand and I was sad about it. When I grabbed for his, I knew he was winning me over.  The day before I was certain I'd break his heart. He asked my plans for the rest of the week and I gave a noncommittal response. Part of me was still guarded.

We did chat the following day and he shared epic high school flashback photos. I'm pretty positive that my 16 year old self would have had the biggest crush on the kid. Besides, he was an all-state soccer goalie and that's pretty much what mattered in high school. So much for him being unathletic. I stayed up past my bedtime to continue our conversation and asked if he was still free the next day.

If you're keeping count, that'd be three dates in a week. A work week to be exact.

He showed up at my house the following day and I couldn't believe how attractive he was. I don't know how I missed him being so handsome the first few times. And when he raved about my favorite pizza place, I knew he had taste too.  After dinner, we sat on my couch talking for hours. I stayed up way past my school night bedtime again because being with him felt more important than sleep.

I think I caught the feelings.

Don't Call It A Comeback

After the ending of date one, you'd think that I'd be done with the guy, but he left his sunglasses at my house. I see what you did there, sir. I HAD to text him. Luckily, he texted me first.

We continued to message on and off for the duration of the day and I found myself amused by our conversation. I even suggested meeting up for a drink after my earlier plans. He did. He also reminded me that I agreed to a second date. Doesn't this count?

Meanwhile, I tried to schedule a first date with someone, anyone else. Due to my travel schedule, I couldn't work it out and when the guy asked to see me over the weekend, I was obviously free. I suggested a fun! architectural tour because summer in Chicago. He was nice enough to offer getting tickets the morning of so we'd be guaranteed a time slot. (The planner in me smiled). I met him and he mouth kissed me in the street to which I was a bit taken aback. When he tried to hold my hand on the walk, I tolerated it briefly. I kept thinking to myself that I was bound to break his heart.

We enjoyed the boat ride and commiserated about the unremarkable tour guide. He provided his own fun facts that he remembered from a previous tour as I enjoyed his company. We were both famished post-tour so we decided on a patio lunch. He kept asking about my evening plans (I was supposed to meet friends) and I kept responding that I didn't have to go. For whatever reason, I wanted this date to go on.

And it did. After lunch we went to an arcade and made silly bets on games. While I perceived him to be athletically inept, he beat me handedly in arcade basketball and won himself dinner that week. I was nonplussed- wasn't one date in a week enough? Besides, the jury was still out on him. That didn't cause me to go home. We instead went to his terrace to play bags and bullshit. All the truth serum in me and I revealed I only dated guys with graduate degrees. Don't worry, I threw up a little typing that just now. The guys with graduate degrees weren't on this date with me and I thought to myself, maybe I should just say fuck it my checklist. *to the friends who've preached this, you might be right*

Date two lasted for 11 hours. Date one lasted for 6. I mean I at least enjoyed his company.

I Was On A Break

Apologies for my 4 month hiatus from posting. Date 2 (reread if you need a refresher) followed by dates 3-6. Because I was actually interested in this guy, I didn't feel a need to go on other dates. Due to busy schedules for both parties, these consequent dates occurred over 3 months. While I would have liked more time in-person, I thought enough of the guy to keep him on the radar. One day every three weeks does not constitute a relationship. I think I fooled myself into thinking that if I was patient, it'd all work out like it should have. It didn't. The last time I saw him was sometime in May and I had very lukewarm feelings; I remember gossiping with girlfriends about all his shortcomings and realized that I no longer liked the guy. Turns out, the feeling was mutual. While I would have preferred to be the one who initiated the end-it text, I responded with, "well, that's a relief." Because it was. 

I enjoyed my single lady status but making eyes at a sexy MBA at a wedding. Turns out, he did not appreciate all things glow sticks so I deemed him boring. I talked to the married groomsmen knowing that the conversations were all innocent (until the one offered to walk me home in between his bumble sessions...). I was asked to join a single groomsman in his hotel room, but I politely declined. Maybe I've matured in my 30's because why else would I turn down an opportunity for a makeout?? To my friends who have known me for years- am I right?

After a month off, I decided to get back on that dating train. I met a guy for Friday happy hour and went into the date with zero expectations. That said, I ordered a tequila drink off the bat because WHY THE HELL NOT. When he arrived, I knew this wasn't going to be the love of my life, but he seemed nice enough. It was a gorgeous Chicago summer afternoon and patio drinks were in order. I can't recall what we discussed, but I wasn't trying to escape mid-first drink either. He did not look like most of his pictures and I found myself wondering if I was on a date with the "personality" guy. When we moved to the shade, however, he took off his sunglasses and I took a double take; he had gorgeous eyes. That plus the tequila had me agree to dinner and a second location- this date was already exceeding my first date duration standards. 

Over tacos and more tequila (I did not stick to my two drink limit, I wasn't hoping for a second date), the conversation flowed easily and I think I even asked him some personal questions. He told me that this was the best online date he'd been on (slay) so we kept it going. I even invited him over for some porch sitting and when he walked into my decidedly messy apartment, I couldn't care less. Another date wasn't in the cards, but a tipsy makeout just might have been. He asked me how he was doing on the date and I told him a solid B-. He took it with grace then pressed for more. While the truth serum was flowing, I might have said something about him being cubbier than a few of his pictures. He laughed. 

Even later in the date, he insisted that he'd be going home because he wanted to go on a second date with me. I was in the complete opposite camp on those issues. Can't a girl have a makeout and never have to see the guy again?  I begrudgingly agreed to the date knowing that I'd have a easy text out at a later time.  Back in the dating game. 

The Good Ones

The weeks went by and I have to admit that I thought about the guy often. We didn't have a text relationship though with a date two in sight, I felt secure. I also received an unexpected late night text commenting on the merits of our conversations. By the time the date was approaching, I reached out and inquired about plans and he responded a day later saying he'd figure something out. Not seeming too eager, I replied a few hours later with a recommendation. This was the day before the date.

On the day of, I still hadn't received a reply with a place or time. I slowly started to panic. The ball was quite clearly in his court and I didn't want to press the issue if his feelings went in another direction. I waited. And waited. And waited some more. Nothing. My granny bedtime was approaching and I had heard nothing about the night. I have to admit that I was pretty upset; even the gym couldn't console me. I went home and started to dig my plot in my front yard. Here lies Promise. Died in the emptiness of an unsent text. I listened to Adele (lord, bad choice) and when he finally reached out an hour before he expected to meet, I was beyond bitter. I didn't want to go, but I wanted to rip the band-aid as soon as possible so I could move on.

En route, I stewed. Arriving early at the restaurant, I stewed. This asshole had it coming. He showed up in a suit, straight from the office. That anger? Subsided almost immediately. Did he have to wear a suit so well? Looks aside, he relayed his hellish work schedule that week and I commented that I was surprised we even met. Based on the timing of his text, I was already mourning his loss. He countered with, "we made a plan weeks ago." Ok, yes, he had a point, but how often are women disappointed when a guy doesn't follow through? I suppose my prior experiences already set him up for failure. He genuinely wanted to see me and though he had a particularly intense week, he made the time.

Don't worry, I didn't let him off the hook for the poor planning. He assumed my text asking about work time meant that we'd be meeting after 8. I said I was waiting on a time and place. I guess we're going to have to get to know each other's tendencies at some point. With his hand on my back, he assured me that seeing me was important. I let that guard slip again and said that I was only disappointed because I had looked forward to seeing him. Being mutually transparent is so refreshing.

We finished dinner and continued our date at a bar nearby. He was so easy to talk to that I spoke my mind freely and we even broached the all-taboo politics topic. He looked at me seriously and gave me the most important compliment I could ever receive; he told me I was one of the most intelligent people he's met. I cannot fully represent the weight of his words. He then verbalized everything that he intuited about me. And he was spot on. It took my therapist years.

As we continued, he asked me when we'd move on from a cheek kiss (date 1). I was taken aback. I lacked all ability to hide my blushing emotions and he followed asking me about kissing in public. Now, college was proof enough that a good bar make-out could rarely be missed, but in my older years. I generally avoided it. Till then. After a totally tasteful kiss, I found myself grinning. There went that rule.

He asked about my weekend plans and scheduled our next date. I stayed out till almost midnight on a school night. Did I like this guy? The post-date sidewalk kissing session certainly implied so. I couldn't stay mad. At all.