Hey Boys, Here’s How NOT to Get A Second Date


Since I’ve been single for forever I’ve had A LOT of time to rack up an accumulation of cringeworthy dates. You know, the kind where you vow to not date again for 6 months minimum? Some are awful right from the get-go and some just slowly evolve into a bad dream. And the worst part is you usually feel trapped by the fact that he paid, he drove, etc. and don’t feel that it’s polite to end it right away. So you suffer in agony through his dull stories and bad etiquette until you have had enough martini’s to soften the irritation building in your brain. 

For me, you get one try for a date and if I’m not super interested, or at least on the fence, then it’s over. And I have had one and done’s with the majority of guys I have been out with. I don’t feel like my standards are too high either. Just be cool and don’t be a douche. Those qualities should not be as hard to achieve as they have been. 

I always give a guy props though for having enough balls to approach a woman and ask her out (especially to dinner and ESPECIALLY if he calls instead of texts), so even if I don’t feel a spark right away I will give him credit for that and say yes. So dudes, if you get the date and you really like the girl, DO NOT do any of the things in these following examples. Kthxbai. 

Bad date #5

I was walking down the hallway of my apartment building after a long night at work, looking sweaty and shiny and tired, and I ran into Jarrod* who was taking some garbage to the trash shoot. Jarrod was this guy who I had run into several times in the elevator hallway and exchanged a polite hi, but that was it. He stopped me dead in my tracks by grabbing my arm and saying, “Hey! Do you want to go out sometime?” I was so caught off guard that the only response I could give was yes.

I gave him my number and regretted it immediately. He proceeded to text me about every 20 minutes from that night until we went to dinner about 4 nights later. “Hey! Good morning! What’s are your plans today?” “You’re so amazing! I’ve wanted to ask you out for months!” “You seem super fit. I’m actually really lazy and kind of a dork. I must warn you I really like fantasy football (actual text)” I mean, are you serious? All day text convos are designated only to my BFF and my Dad, if he even wanted to do that, which he doesn’t. 

Anyway, I still decided to give it one shot and went to dinner with him at a cute Italian restaurant. He received major brownie points from me for dressing suave, smelling nice, and having a good solid job that he explained to me all about. But the night took a huge left turn when he said, “After my ex and I broke up I’ve decided that I just really want to be honest about everything.” And he proceeded to tell me how amazing I was after almost every sentence I spoke, that I was so beautiful that it made him sweat and feel nervous, and that I’m so cool and awesome that he isn’t sure if he even deserves me because he is the biggest nerd ever. TONE IT DOWN, desperate! Jesus. I seriously had to say to him, “You know, some things are better in your head as thoughts than actually made audible. You might want to leave some mystery.” And he went on and on about how he’s no bullshit and I’m sorry if that scares me away blah blah. 

So guys, don’t be like Jarrod and reveal WAYYYYYY too much too soon and come on WAYYYY too strong. I mean, this dude didn’t know me at all. It was like he had been dreaming and fantasizing about me all day and night and had come up with this untouchable princess fantasy in his head. Yikes.

Bad Date #4

David* was a guy that I met while getting some late night grub at a diner. He was working behind the counter and he was just all charisma and charm while I waited for my to go food. He told me he was a student, so I figured the fact that he worked at a diner wasn’t the WORST thing ever. He got my number and we set a date to see a Shakespeare play, which is a perfect date idea for me.

While we were texting during the day of the date he slips in there that he wants me to drive. I was like, “Okayyyyy.” And he says, “I would, but I don’t have a car.” I was immediately thinking of canceling, but then I decided I really wanted to see the play. So I picked him up at his apartment and he told me he would navigate us there. He failed to tell me though that the theatre was in MALIBU, which is QUITE a trek from Hollywood, especially during rush hour. My car at the time was a 1997 Mitsubishi Galant, which is not nearly as glamorous as it sounds, and didn’t run very well. It also didn’t have cold AC, but it was about 150 degrees that day, so I was running it anyway. I was anxious the entire way there that the poor thing was going to break down.

The play was good, the conversation to and from was bad. He was very into himself and his “acting” and wasn’t the sharpest tool in the shed, complete with really bad grammar (total buzz kill for a writer). I thought we had found a common interest when he started talking about Al Pacino, but then mentioned “Goodfellas” which stars ROBERT DENIRO YOU IDIOT and it was all over with.  

It’s totally fine if a guy doesn’t quite have his shit together yet, but if you’re going to date people, suggest things that are cheap and fun and easy! However, the lesson here is: NO CAR? NO 2nd DATE. Sorry. Oh, and also, don’t be dumb. 

Bad Date #3

I met Greg* at The House of Blues one night to see my friend’s band play. He was cool and funny and tall and had a really nice confidence about him. He was a ginger though, which is SO not my style (I’m only half kidding). We agreed to meet at this piano bar on a Friday to drink and listen to some tunes. Well, here’s a warning to everybody: at a small piano bar you will NOT be able to hear your date. There were so many “what?”‘s and zero recognition head nods that finally we decided to go somewhere else.

I wished that we had stayed where I couldn’t hear him because once I could, I realized that he was a sexist pig bordering on misogynist. He told me all about these comedic YouTube videos he’d done of original rap songs, and his latest creation was called, “Don’t Feed My Girlfriend”. This genius work of art is about how he doesn’t want his girlfriend to get fat, so he asks others to please not give her food. In the video he has his girlfriend on a leash. I can’t make this shit up. I have a pretty high tolerance for offensive humor, but the video isn’t even good nor is it funny. It’s trash. The worst part of it was that he decided to give me a little “preview” of the video and rapped live for a veryyyyy uncomfortable 30 seconds. Like, no.

So guys, if you want to get a second date with a girl, make sure you keep all offensive video projects secured on YouTube or Vimeo with a super secret password so that she can’t find them for at least 6 months. She’ll probably find out that you’re a pig before then, but just in case.  

Bad Date #2

Matt* was a guy who I met out at a bar one night. I rarely give my number out at bars because I’m usually wearing beer goggles, but Matt made me laugh SO hard that I figured I could make an exception. He was pretty cute and spoke with a Southern drawl which I found made him seem even funnier. As soon as I got home that night he called me and we talked for almost 2 hours and I cried from laughter at his dumb one liners.

Our first meeting was at a bowling alley/bar in Hollywood that had late night karaoke, which is my favorite. He said his friend and his friend’s girlfriend would be joining us too, which I was fine with. I arrived at the bar and found them all outside smoking weed. I was like, “Oh hell, let me start drinking to be okay with this situation.” Once we came back inside we went upstairs to the karaoke room instead of bowling any games, which was weird to me. I suddenly realized that his friend, the girlfriend, and possibly even Matt were on some hard drugs. The girlfriend especially was totally on some other level and screeching into the mic when she got up to sing. I take karaoke very seriously and when I got up to sing I was going to show them all my chops and stupid friend and girlfriend took the other mic and sang with me, completely ruining the song. After doing this on my song #2 I just gave up and took a seat halfway through.

Matt finally realized that I was uncomfortable and wasn’t very surprised when I wanted to leave. He walked me to my car so slam hammered that I had to help him walk straight. I told him that I wanted to give him a ride since there was no way in hell he should be driving, but he wouldn’t take the offer. So we’re standing there talking and all of a sudden he smashes his face into mine and gives me the most awful, slobbery kiss ever with a mouth that was stale with the taste of beer and cigarettes. So, pretty much the least enjoyable kiss of all time. That was the last I saw of Matt.

Okay, so the lessons here are numerous but the biggest one being DON’T BE AN ALCOHOLIC and/or DRUGGIE.

Bad Date #1

Max* was a guy who was my server at my favorite local bar. Immediately he was enamored of me. He took such an interest in finding out about my life and who I was and was very attentive to my needs, whether they be food and drink related or not. He was convinced it was love at first sight and got my number. 

He would send me sweet texts here and there and one day wanted to see me at his bar around lunch time. He said that I should pick him up an eggnog latte from Starbucks on my way over. I couldn’t believe he would ask me that, and I joked around saying, “Whoa, I’m not your girlfriend yet.” He was not amused. Needless to say, I did not visit him that day. 

I did still go on the date though. We decided to have a picnic date in a park, which I thought was really different and cute, and before we headed over to find a spot he told me to pick a nail polish color out of the 4 he had in his hand. I thought he was giving me a gift and was so flattered. I chose the robin’s egg blue color. As soon as we sat down with our stuff he took off his shoes and socks and told me to paint his toenails. I was totally grossed out, but thought maybe it was like some weird fetish thing he did with girls he liked. Whatever. The lunch conversation began with him telling me he could see himself marrying me, but then 3 minutes later told me he was leaving in a week to do a charity run across the country for 3 MONTHS. Wtf?

After the picnic we went to walk around The Grove, which is an outdoor shopping center. It was decorated so beautifully for Christmas and he stopped 2 or 3 times to ask me to take pictures of JUST HIM in front of pretty decorated areas. After that he asked me if I wanted a chocolate dipped banana, and I was all, “definitely”. He ordered one too and then proceeded to tell me, “since I paid for lunch it’s your turn to pay.” I was completely turned off, but I did it. Who says shit like that?

Day turned into night and we went to a Mexican restaurant for dinner. After eating (and splitting the bill of course) he asked if we should watch a movie. My Wednesdays are very sacred to me and I have a bar I always go to with my friends and I told him this. He then says, “I cleared my whole schedule for you. That’s not really cool if you ditch now.” I mean apparently 8 hours is not enough time to give someone anymore. 

I decided to take him to my place to watch a movie. We looked On Demand and chose the movie he wanted to watch, of course. Afterwards we started making out (only because of the copious amounts of wine I had) and he asked to move to the bedroom. Normally on a first date I never let it get there, but my roommate had just gotten home so I figured it would be better for her. 

I can’t believe I’m about to tell you this next part…

We start really getting into the making out and we’re, ya know, dry humping, and sometimes girls can get (ahem) a little aroused by this sensation, which is exactly what happened. He stopped for a second after that and said, “now it’s my turn” and unzipped his pants. Seriously, I should’ve kicked him out right then for being so gross and forward but I didn’t. I gave him the driest, worst, most un-inspired hand job of my life just to give him what he wanted so he would leave. I felt so used and disgusted. It was like some kind of mental sexual assault. 

Guys, please don’t EVER do any of the things this guy did. Not only did he not get a second date, he got an earful to all of my friends and a blog post about how he is the worst date ever. Congrats, douche. 

I hope soon I won’t have to go on any more bad first dates because I will be in a relationship. One can dream, right?

Not all guys are stupid though and so my next post will feature my top 5 BEST dates. 🙂


*all names changed, duh

2 thoughts on “Hey Boys, Here’s How NOT to Get A Second Date

  1. I love your posts because I can honestly say I relate to them 100%. I’ve been through every scenario you’ve been through with the guys. I’ve been single for almost four years and I’m slowly giving up…guys aren’t like they used to be.

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