Ten

Last year my sister set up an OK Cupid account for me – she said she was bored, but truth is she never wants me to move away from her, so she thinks if I find a man in SF I’ll stay forever (so far she's out of luck).  I kept the account for about two months before canceling it because (a) since I'm not looking for "the one" I didn't really care, (b) apparently you have to be on there all the time to make things happen, and (c) I found that I get awfully "judgy" when I'm looking at people's dating profiles (whether it's their choice of picture, their grammar, or their hobbies) and I don't want to be a jerk like that.

Believe it or not, I'm not always social.  On occasion I decide to be a hermit because maybe I'm dogsitting and choose to be lazy or perhaps my face is having a horrible week and doesn't need to be seen by the world.  For times like these I decided to re-activate my Ok Cupid account so I can still ask out a guy while simultaneously lounging in my pjs and eating chips & guacamole.  A few days after I was back on the online dating circuit, Ten rated me a 4 out of 5 but didn't make any further attempt to contact me.  After checking out his profile and seeing that among having a few other things in common, we both love the Goonies.  I sent him a message that was simple and to the point, “If we both like the Goonies, it probably wouldn't be a disaster if we met. What do you think?”  I have yet to get a response from Eleven, which makes me sad because my follow-up question was going to be "Hey, why did you only rate me a 4 out of 5?"  How on earth will I know how to improve myself to gain that last point now?

Update

In case you are keeping score, I sadly have only about 1% progress to report.  So much effort, so little reward.

One, Two, Seven, and Eight were no-go’s.  I even went the extra mile with Eight and posted a Missed Connection on Craigslist, but I didn't get any response.  I never heard from Three or Four.  Five was supposed to call me when he was back in town, but I never heard from him; clearly he never came back from Hawaii. 

I think Six and I somehow merged right into friends.  He texted me the night I gave him my number so that I would have his number, and then we became Facebook friends.  I didn't get to see him on Halloween so he texted me a picture of him in his outfit, in which he was wearing a red thong - hilarious (with the cape and horns, his costume was a "sexy devil").  We chat on Facebook regularly about nothing in particular.  I’ve invited him to do things a few times, and he’s always very apologetic about not being available.  However, he did make me an amazing mixed CD before he left for the Christmas Holiday, so in middle school terms, I’d say we’re an official couple.

Sadly I never heard back from Nine.  After my initial text about going on a date, I sent another text a few days later inviting him to meet me out dancing.  Obviously his phone must have been stolen after we exchanged numbers because I never got a reply from him.

Stats:

- Nine attempts

- Zero dates

- One new friend with great music taste

- Tons of entertainment for you and me

- Nine guys out there who hopefully have a rise in their self-esteem

Bring on the next one!

Nine

I found my energetic, dancing counterpart!  Nine was all over the place on the dance floor, making friends with everyone, while his friends just watched in embarrassment from the sidelines.  That’s my style..dance like crazy and talk to strangers while my friends stand aside just shaking their heads at me.  Yes!  To top it off at one point Nine caught my eye and reeled me in with the fishing move.  Destiny.  He was totally obnoxious (but in a fun, goofy way) and had a loud East coast accent.  Nine confessed his love for Salt ‘N Pepa, and I’m pretty sure he fell in love with me when I told him sometimes I do "Push It" and "Shoop" at karaoke.  I repeat, destiny.  I was having so much fun that I told him, “Get your phone out.  We’re trading numbers, and we’re going out.” After the number exchange he gave me a kiss on the cheek and said, “I’m your guy.”

Now I will admit that by the time we exchanged numbers, Nine was a little tipsy, and in case he forgot that he had my number I decided to make the first attempt at reaching out a few days later.  Most of my life I have been told that I can be intimidating, and sometimes I listen to people’s advice (but most of the time I say, “I am what I am” and do things my way).  With Nine I decided to compromise.  Normally I would call the guy, but I decided I’d be modern and text him instead to be a little less forward I suppose.  Three days  later (because three days is the rule, right?  I hate the rules and usually ignore them, but I’m trying here) I sent him this text, “Dancing was great!  Now let’s follow that fun up with a date.”  I’m trying to be clear about this whole date business because I have a tendency to go from flirt to friend in about .04 seconds.  It’s a fine (or maybe just invisible) line for me when it comes to being intimidating, friendly, and a flirt.  We’ll see what Nine thinks.

Eight

Some friends and I were out for the night listening to some bands.  While waiting for the main band I told them, “I’ll be right back.  I’m going to go ask a guy on a date.” Then I walked up to a guy that earlier in the evening I shared a 30-second conversation regarding a song that had been playing. Now I wouldn’t say I have a definite type, but a few of my friends definitely say that “The more homeless a guy looks, the more Penelope likes him.”  Taking that into account, I’m trying to be diverse with these attempts.  This particular guy was wearing a plain, button-up long sleeve shirt, had a grown-up haircut, and just a tiny bit of scruff.

I did what I do best, and just walked right up to Eight and started talking, “Hi again!  I have a few personal questions for you.  Do you have time?”  Seeming to be amused by my frankness, he said sure.

“First.  What’s your name?” “Eight.”  “Eight, I’m Penelope, it’s nice to meet you.”

“Second.  Will you be growing a mustache for the month of November?” “Absolutely, I’ve already started,” insert the beginning of me giving him a high-five as he continues, “My uncle actually recently died of prostate cancer.”  Stopping my high-five in mid-air I said, “Oh man.  I’m totally taking back  that almost high-five and giving you a hug instead.”  Insert totally comfortable hug here and then my non-existent transition to the next question. 

“Next.  Now this one’s really important…if M&M was to discontinue all M&M’s but one kind, which one would you insist they keep?”  Without hesitation Eight replied, “Green.”  Laughter from me, “I meant, you know, peanut, plain, almond…”   Eight was adamant, though, “Nope, just green.  They can get rid of everything as long as they keep all the green ones.”  “Wow, I love that answer!  That leads me up to my last question.”  He teasingly told me, “Well you’re already up to three questions, but I guess I’ve got time for one more.”

Without missing a beat I went for it, “If I were to give you my number and asked you on a date right now, would you call me so we could go on said date?”  At this point, I’m pretty sure he thinks I’m the most entertaining person around as he laughs and says, “What?! Do people still date?  Because I don’t date.”  I was not giving up, “Well you should start!  Let’s go on a date!”  He was awesome and was totally going along with it, “Hm, let me think about this. When would we go on this date?”  I told him,  “Anytime.  Except tonight that is; this, right here, doesn’t count as our first date.  Ok, the band is starting.  I’m going to dance, you have fun, think about it, but don’t leave without getting my number okay?”  “Deal.”  I don’t know if he fled or what, maybe he looked for me, but I didn’t see him when the show was over.  Argh, I liked our rapport, and we seemed to have great date potential in our 5-minute conversation.  Lesson learned here - follow-through is key.

Time Out

Here I am asking out all these guys, and I haven't been asked out on any dates since I started this blog.  However, I don’t want you to feel sorry for me because even though I might not get asked out all the time, it does occasionally happen.  For example, about five months ago, a guy in my neighborhood asked me out.  He was sweeping the sidewalk as I walked by, and our interaction went something like this...
Guy: Hi there, pretty lady, how are you doing today?
Me:  I’m doing great.  How about yourself?  
Guy: Oh, I’m all right.  Listen, would you want to get a bite to eat with me?  
Me: I’m sorry, I'm on my way to work.
Guy: Well, it doesn’t have to be right now.
Me: No, I really can’t.  I don’t think my boyfriend would like that very much. 
Guy: Oh, I see.  Well he’s a lucky guy.  Could you spare a dollar or two for me instead then?


Key pieces of information here: I lied to him about having a boyfriend and the guy is a semi-homeless men.  He’s always nice and clearly clever because I felt so bad about turning him down (and lying about having a boyfriend) that I gave him money for lunch.  So yes, sometimes, I get asked out, kind of.

Seven

“Those are some sweet legs,” said Seven, the young, clean-cut, business man standing behind me in line at the bagel shop.  I’m smart enough to know that he meant the legs on my earrings – I have these amazing pair of earrings that are laminated pictures of legs in high heels that touch my shoulders, oh, and one of the legs has a guitar strut down it.  They are a great conversation starter, like today.  As we stood in line, we bonded over my accessories, his speedy bagel-ordering abilities, and the great weather (he was taking advantage of the sunshine by skipping work the next day to play frisbee golf).  We got our orders at the same time, and when we walked out I decided to seize the day! 

“This was fun.  Would you maybe wanna go out sometime?”  A flicker of surprise definitely crossed his face before he replied, “Um, what?  Thanks, but I can't.  I have a girlfriend.” I was totally unphased and just said, “Oh, ok, well have a good day.”  Seven apparently needed some closure, so he followed up with, “Um, oh, wait.  Did you think I was hitting on you?” I could tell he was not being a jerk, and was just concerned that he led me on, so I told him, “Nope.  You were nice, and I figured why not?  I mean, you definitely shouldn't stop being nice to people because of this!  I swear they won’t all try to ask you out like I just did – and I totally don’t mean that in a rude way.”  After a nervous laugh from Seven, some more “ums,” “ohs,” “have a nice day,” and “see ya around” I walked away laughing to myself.  I might not be getting any dates, but as always I love the absurdity of my life.

Six

I'm a receptionist at a hair salon, and there are definitely a few guys that come in that make me giddy.  One of these guys is Six - adorable, artsy, and super friendly.  Whenever he calls or stops in the salon, we talk like we’ve known each other for ages.  I’ve had a crush on him since the first time he came in, but there’s never been a good time for me to ask him out because I’ve never seen him outside of the salon, and it seems a bit wrong to ask him out while he’s paying for his haircut.  I mean, I guess I could always get his number from our client file, but (a) that’s probably unethical and (b) it’s definitely creepy.  I’m not trying to become unemployed or a stalker here. 

Today he came in for a cut, and we talked about Halloween costumes and plans while he waited on his stylist.  I decided there was never going to be a perfect time to make my move, and his appointment was one of the last ones of the day, so today was the day.  There were two stylists there – Sara and Kim – and another regular client, Scott.  In my mind it was going to be as near as perfect as possible – Kim would finish Scott’s cut first and leave and then it would just be Sara, Six, and me left, and Sara knows that I like Six.  Of course, that’s not the way it went down.  Sara finished first and the three of us talked for a few minutes, and then Sara wandered away while Six paid.  He and I kept talking, and I wrote my number on a post-it note for him about the same time Kim and Scott finished.  Scott came up to pay, and then apparently noticed I was in flirt-mode because he walked back over to talk to Kim while she got ready to leave.  The two of them and Sara were just hanging out five feet away waiting on me because they were all ready to leave, so I sped up things by handing the post-it note to Six and saying, “This is for you.  Definitely hit me up and we’ll go out.”  So eloquent and romantic, I know.  Six looked at it, smiled (genuinely, I think), and said, “Thank you so much. Seriously.”  When he walked out Kim, Scott, and Sara were just laughing at me while I thanked them for giving me time to hit on the client. So not the ideal situation, but it happened.  

Five

Background: My niece goes to a daycare run by a Ukrainian lady named Ella.  The other day Ella told my sister, “I have a man for your sister.  He is handsome, tall, and a professional.  I was going to set him up with another lady, but she has three kids, so I think it is too much baggage.  So he is for your sister.  Here is his email address.”  Let me be clear, my interactions with Ella are limited to “Hi, how are you, thank you, see you tomorrow” twice a week when I pick up my niece from daycare.  Basically I have nothing to lose with this potential match-making attempt, so why not?

To: Five

From: Penelope

Subject: Hello from Ella’s friend

Hi Five!

My niece goes to Ella’s daycare, and Ella thought you and I should meet.  My schedule is all over the place these days, but I’m definitely up for meeting you sometime.  Let me know if you would like to meet.

Penelope Jones

415.555.7949

A few hours later I answer a phone call from a blocked number, which turned out to be Five.

Me: Hello

Five: Is this Penelope?

Me: Yes

Five: Penelope Jones?

Me: Yes.  Who is this (insert confused tone here)?

Five: This is Five.  You sent me an email today.  So how do you know Ella?

Me: Oh, Five, hi!  Yeah, my niece goes to Ella’s daycare, and Ella told my sister you and I should meet.

Five: Oh, well, I talked to my sister-in-law when I got your email, and we thought it might be a scam of some kind.  I didn’t realize Ella had my email address, I don’t know how she got it.  So you live in Lafayette then?

Me: Lafayette?  No.  I live in the city.

Five: Oh, then I don’t understand how you’ve met Ella.  She doesn’t have daycare.

Me: Um, yeah, the daycare is in my neighborhood.  Um?  I’m not sure we’re talking about the same Ella.  Ella is the Ukrainian lady who runs the daycare.

Five: What?  Oh I don’t know who that is, but my niece is Ella.  (Insert our combined confused laughter here).  So I’m not sure who your Ella is.

Me: Well, she’s a Ukrainian lady that runs the daycare where my niece goes.  She gave my sister your email address.  I think maybe your mom and her mom know each other?

Five: Wait, is she Russian?

Me: She’s Ukrainian, but yeah she speaks Russian.  (haven’t I already said Ukrainian a few times?) She’s short, round, and has dark short hair.

Five: Oh, Evalina!  Wait, should I be calling her Ella?

Me: Since there’s a chance we still might not be talking about the same person, I’d say you should keep calling her whatever you’ve been calling her.

Five: I guess so.  Now that this is all kind of cleared up, thanks for reaching out to me – I'd love to meet you.

Conclusion: Five is going to Hawaii for a week, but he’s supposed to call me when he’s back to set up a time to meet.  We’ll see.  Oh, Ella/Evalina.

Four

Apparently I have a penchant for writing notes to guys.

Exhibit A: Attempts 1 & 3. 

Exhibit B: A few years ago I met a guy at a friend's wedding, and we started hanging out regularly. I decided I might like him, but I couldn't read his mind to figure out what he thought about me.  My method of getting to the truth?  Writing an email for crystal clear clarification – in my professional opinion people are more honest on paper since they don’t have to look at the other person while laying it all out there (plus, you get written proof if you need it for your scrapbook).

To: The Crush

From: Penelope

Subject: The deal, middle school style situation

I like you, but since I haven’t been able to meet up with you lately, I haven’t had a chance to share that little secret with you.

Possibilities:

1. Maybe you’ve got a gal and can’t be bothered with me

2. Maybe you like me the same as I like you, and you want me to kiss you so we can see what happens

3. Maybe you have absolutely no interest in me and never want to see me again

4. Maybe you’re free and single and just want to keep it that way

5. Maybe you think I’m cool, but you’re only interested in friendship

6. Maybe you like me, but you think I want to go steady and you’re not looking for commitment

7. Maybe something else that I haven’t covered here

Conclusion:

Are any of the above true?  #2 is my top pick, but I’m really okay with any of them (except #3.  If you choose #3, can I get my Hello Kitty Tupperware back before you tell me to go away?)  Be brutally honest; I can take it.  I really want the complete truth rather than not knowing.

To: Penelope

From: The Crush

Subject: Re: The deal, middle school style situation

LOL, middle school style, ok, let me look these over….#1 except that doesn’t mean I can’t hang out with you.  #4 but we aren’t officially together. #5 I do think you’re a cool girl, seriously, but I don’t see us as more than friends.  I like kickin’ it with ya, but just as friends if you’re cool with that because I really do have a good time with you.

Fast forward to now: The Crush and I are still friends, and I’m still writing notes to guys.

Exhibit C: First of all, homemade chocolate yogurt sprinkled with graham crackers – yum!  Clearly Four, aka the guy working behind the frozen yogurt counter, and I had a connection when he asked me what my shirt said and I read it to him “Indie, Pop, Rock, You, And Me” (I attempted to flirtatiously emphasize the “you” and “me” portion).  I asked my friends how old they thought the guy was, and Polly pointed out his mustache as proof that he was probably old enough.  You should know that I am horrible at the age game, and it’s always better for me to get second opinions on the age factor.  With their just barely age approval, I went back to the counter for my mission.

Me: The yogurt was delicious, and this is for you (as I handed him a note)

Four: What’s this?

Me: You get a love note today!

Four: Is it from you? (with an adorable smile, which made me think, “Oh my goodness, this is a frozen yogurt place, this dude’s got to be crazy young.”)

Me: Yep, bye!

The note…

Dear You,

You seem like you are most likely a nice fellow.  Fact:  I’m pretty fantastic myself.  Conclusion: We should go out sometime.

Sincerely,

Pop, Rock, Indie shirt girl (aka Penelope) 415-555-7949

While the note might not work with this kid (I say kid because in retrospect I’m convinced that he was a youngster), I might start carrying generic notes to pass out because really I never know when I might need one!

Three

I love karaoke!  For my birthday, my friends and I went to karaoke where I like to think I wowed the audience with my rendition of “Shoop.” My sister made a chocolate cake for the occasion, and when it comes to chocolate, I must share it otherwise I’ll eat it all by myself in record time.  Therefore, I had to offer it to the guys at the table next to us.  Earlier my friends and I were playing the game “gay or hipster?” (rather than "gay or European") and if the guys were hipster, whether or not I should ask out one of them.  I decided they were hipsters, but remember typically hipsters don’t love me because I’m always decked out in colors and have an over-the-top cheerful personality.  Apparently cake (or maybe my dress made from Star Wars sheets) is the uniting factor of our worlds, though, because after cake was shared and songs were sung, our tables were chatting.  I had my sights on the tall, skinny hipster (complete with skinny black jeans, flannel shirt, and sketchy facial hair), but it was a tough decision because another possible reason I don’t often have luck with guys is because (1) I never know which guy to focus on in a group and (2) I don’t want to pick the one that always gets picked because then I feel badly for the others (egotistical or do I just have a bleeding heart?).  Three was the tall, skinny one and he hadn’t sung yet; he informed me (when I asked if instead of a singer was he the back-up dancer?) that he was the encourager and supporter.  In the midst of our conversation I handed him a song request that I filled out earlier and told him, “Here’s a song request for next time.”  Without so much as a glance at the paper, he said "Okay" and walked away looking slightly confused.  The request:

Name: Penelope

Song: I WANT YOU TO WANT ME

Song #: 415-555-7949

Key: It’s my birthday week - let’s go out!

The evening went on without any awkwardness and was full of more singing and dancing.  As the guys left they told us goodbye and that we should come by there on a Sunday with them.  After they left, we saw a folded up karaoke slip on our table that said “SONG REQUEST FOR NEXT TIME”

Ph(F)ilomena, You are offensively beautiful, stop that.  –Three 415-555-1342

Um, my name isn’t Philomena or Filomena, that’s one of my friends that was with me.  Seriously, dude?  You either (a) aren’t the brightest because I wrote my name on the paper I gave you (b) aren’t clever enough to ask my friend out using a different method than the one I used on you or (c) are a jerk.  My friends were all “Oh I bet he just mixed up the names.”  Whatever, I wrote my name down for him, so he should have double-checked.  I’m not an emotional sap, and in the end it made the story funnier to me.  I’m not calling him, though; I gave him my number first, and because I don’t want to see his sad face when I walk into “our” date instead of Ph(F)ilomena.

Two

This weekend there was a giant music festival, so I was a complete slacker about asking out anyone because I knew the park would be full of guys for my cause. True and false. The park was absolutely full of guys, but I now realize a music festival is not the ideal place to go up to a guy and ask them out on a date. Reason 1: men apparently don't often go to music festivals with only other guys. If there’s a guy, there’s probably a girl. I'm sure this has always been the general situation, but I've never noticed it before. Maybe they’re not together, but there is no real way to tell, and I’m not about to go flirt and/or ask a guy out in front of a girl who is potentially his girlfriend and will murder me with her eyes or punch me with her fists. Reason 2: drunk and stoned men in a park during the day are not that appealing. Reason 3: if you do happen to see the man of your dreams and there is no girl in sight, you still have to climb over people sitting down or push through a crowd to get to him, and that’s just terribly inconvenient.

The first guy I decided on fell under reasons 1 & 3. I was going to have to climb over a few packs of people to get him, and by the time I decided that the effort was worth it, a girl in the group walked up to him and hung onto his arm. The second guy I chose ended up being reason 2. He was with two other guys and they were standing in a fairly empty space, so with my friends cheering me on (or laughing from embarrassment for me) I went to make my move. I tried to ease into a conversation with music festival small talk. "Is this the final act for this stage?" Insert caveman-like grunt reply here. "Have you been here all weekend?" Affirmative grunt, I think. "Nice. Who was your favorite band of the festival?" Response of blank stare. I stood there awkwardly (important side note here, even when other people think a situation is awkward, I rarely do, but I did this time) for about 35 seconds before saying, "Ok, see ya" and walking away. I'm filing that one under the category of non-English speaker or totally stoned.

Finally at the end of the day, there was a group of guys that got our attention because one of them was wearing a giant monkey mascot head. My friends (and I’m sure every other smart person there) called him over to be in a picture with us. After the picture, I declared to Monkey Boy (Two), “You’re fun! Let’s go on a date!” Two, “Maybe.” Me, “I’m being totally genuine here.” Two, “Ok,” and then he walked away. I guess his ok was really a no. I really wanted that one to happen because I’m sure it would have made for a great story, and because since I couldn’t see what the guy looked like I wasn’t being one bit superficial. Dang.

One

As pumped as I am about this plan, I decided to ease myself into it by asking out a friend of friends. One is a tall, skinny, handsome guy-next-door kind of dude. He’s intelligent and witty, and I absolutely adore wittiness. I’ve never gotten his phone number, and I only ever see him in group get-togethers where we always make each other laugh. I definitely had a crush on One when I first met him; I have no idea what he thought of me, maybe that I was an energetic loon because the first time he saw me I was walking into a small house party with a container of cookies proclaiming something like, “Hi! I’m sorry I’m late, but I made cookies! I'm Penelope. I think I only know two of you here, so I’m going to need you each to tell me your name and two fun things about you.” True story, that’s how I roll. Since then and our previous group outings, One assumes that I always have an icebreaker ready at any moment. It’s not really my intention, but he’s kind of right. Anyhow, One was in a relationship at that first meeting, but since then he’s been dating around while working on his MBA, so I figure he’s a safe bet. Since I don’t have his number I decided to ask him out via email – so traditional, I know.

To: One

From: Penelope

Subject: Random idea

one! let's go on a date! not like a "we totally have a connection" date, but more of a "we're both fantastic, so why the heck not" date. seriously, let's go on one date just for fun.

i'll be on my best behavior and will even leave my sneakers at home. what do you say?

also, hi and how are you?

I might be horrible at using at capitalization, but at least I’m to the point, right? One responded a few days later…

To: Penelope

From: One

Subject: Re: Random, fun idea

penelope, a smashing idea except i'm way slammed with school and in the midst of a brady-bunch-esque love triangle: i'm thinking about taking two dates to prom but keeping them in separate rooms so they won't know the other one is there, think it will work?

In addition to being witty and sharing my lack of email capitalization, One is also diplomatic. No date, though. Moving on.

The Plan

Ever since college, almost any time I tell a story about an interaction I've had with a guy, my friends laugh and tell me I should write a book. I tell them that my stories won’t be entertaining to people that don’t know me because, honestly, people that don't know me probably think I lean towards the crazy side. Then I came up with the idea of asking out one guy a week for a year. If the guy doesn’t say yes, oh well, it won’t be the first or last time. So yes, this is happening…not because I’m on the search for “the one,” but because why the heck not? Also because of all the guys I’ve kissed in my life, only one of them was my boyfriend. Seriously, I’m a bit of a free spirit and I’ve only had two relationships which both lasted three months – one when I was in 6^th grade (and we never kissed), and the second when I was 31 (we kissed a lot). Instead of going on dates, I usually tend to make out with a guy friend or a random dude that I’ve met. Plus, I moved to SF over a year ago and have even less game here (and by “even less” I mean zero, possibly negative game). I blame it on the fact that the majority of the male population here either also like guys or they are hipsters, and neither of those groups wants to date me. I can’t think of a thing I have to lose with this new plan. I love talking to strangers, I can try different methods of asking out guys, my friends and I will be endlessly entertained, and maybe I’ll actually go on a date (because the last date I went on was with my 2^nd boyfriend over a year ago). Really, the only possible kink in this plan is if one of the guys and I fall madly in love with each other, but hard-headed me forges on with this project and leads a double-life causing all sorts of nail-biting, frustrating chaos to ensue before we live happily ever after in the end (think romantic-comedy with Natalie Portman). Let the games begin!