my latest dating adventures

I met a guy last night for drinks.  He’s a Match guy.  I winked at him, he winked and emailed back.  We made plans to meet after a couple back and forth emails.  I’m not sure what I should nickname him, so I’ll just stick with Mr. Staten Island, because that’s where he lives.  He lives there and works in Jersey, so we met downtown in the Wall Street area.

I am one of those people who hates being late.  It causes me anxiety.  I am 98% of the time early or on time.  Last night I fell in the 2% of being late.  I totally underestimated the amount of time I thought it would take me to get downtown from midtown.  Of course, it doesn’t help that the (local) subway sat at Canal Street for a good 7 minutes, while I’m having mini-panic attacks knowing I’m going to be late.  The train finally pulls away and it’s already 7PM, the time I’m supposed to be meeting Mr. SI (sounds like Mr. Sports Illustrated – hehe).  I get out at the Whitehall St-South Ferry subway and am now at least 10 mins late and I still need to get my bearings and walk to the bar.  Because I am not super knowledgeable with downtown streets, I break out the handy map feature on the iPhone (this app has come in so handy countless times, esp in a car driving) to see exactly where I am and where I need to go.  I finally make it to the bar.

I walk in and see that Mr. SI is sitting at the front of the bar and he sees me and stands up to greet me.  I instantly go into apologetic mode for being <gasp> 15 minutes late.  He’s cool with it and we sit, I order a glass of wine and we start talking.  And we didn’t stop until 2 hours later and another glass of wine later.  I really enjoyed talking to him and found him more attractive in person than in his pictures.  We left the bar and he walked me to the subway.  He gave me a quick kiss goodbye on the lips and I didn’t recoil in disgust (a positive) and thought “yeah, I could totally kiss this guy” (he passed the litmus test).  So, we have plans to hang out not this weekend, as I’ll be out-of-town, but the next weekend.  We’ll see how date #2 goes…

So, I did what many of you may yell at me for.  I reached out to someone who previously was unresponsive toward me.  Yep.  I did.  I have no shame.

The Friday before the Fifth Ave Mile race, I emailed St. Elmo.  We had talked about this race in detail when we had our date at the end of August.  It had been a good month since we last were in contact.  I sent an email asking him if he was running it.  To my surprise, he responded.  He wasn’t running it, but was going to do a long run that day instead.  He also told me to let him know if I was and maybe he could cheer me on at the finish (he didn’t and I didn’t expect to see him).  I wrote back that I was running it and inquired about what marathon he might be doing.  We emailed back and forth about marathons and running.  That was that.

On the Monday after the Fifth Ave Mile, St. Elmo emailed asking how I did.  I actually told him my time, but I’ve already admitted to him my not-so-great half marathon times.  I think he gets that I’m among the slowest runners on earth and told me I’m being too hard on myself (shocker!).  That led to emailing throughout the night and the next night.  He had asked about the weekend, but I am going to be doing fabulous stuff out-of-town – apple picking, baking, eating, drinking, watching football on Saturday and then sailing on the Hudson on Sunday.  We put off grabbing drinks (his idea) until next week because my only free night was tonight, Thursday, and he couldn’t meet.  I originally couldn’t do Friday night as I had one set of plans, but they got canceled (a new set have since been planned for later in the evening) and I asked if he could do Friday after work.  He has dinner plans that he’s going to try to push back.  I’m not sure what to think as he kinda blew me off a month ago and he is super flirty now, way more than last time.  We’ll see how drinks go.  Maybe I just want to make out with him for a bit.  I already know that he passed the litmus test, so maybe at the very least I just need to kiss him and be done with him.

I’ve been trying to keep busy on Match.  I’ve completely given up on OKCupid.  I should just take down my profile.  I made a goal of emailing at least one guy every day.  I also wink like crazy at guys.  Here are a few of the other potential bachelors that I have had actual correspondence or calls with.  There are a couple of guys who winked and I winked back.  If they wink, I’ll wink back, but then they need to email.  And I act the same if I wink at someone and they wink back.  Ball is in my court now and the next step is me emailing:

A lawyer who has Donald Trump-like hair.  He emailed me and sent pictures as he doesn’t have pics up in his profile.  I had to question myself if I could go on a date with someone with Trump hair.  A small pause and then a “hell yeah I can”, if only for the experience of seeing that mop in person! (I’m such a terrible person).  He’s actually not bad-looking.  His face is fine, it’s just the hair.  He suggested meeting next week and I said that works, but have yet to hear back.  I’m not pursuing if he doesn’t.

A widower who reached out to me.  We actually spoke on the phone and his story is that his wife had been battling breast cancer for years and in the past year took a very bad turn for the worse.  They had a baby (through surrogate?  Adoption?  I don’t know, I didn’t pry into that area) who was born at the end of 2009.  His wife passed in April.  He asked me what I thought about the situation – I guess potentially dating a widower.  I said that I didn’t have a problem with it, but my concern is whether or not he is ready to be dating.  He admitted that he didn’t know, but needs to try.  I personally don’t think so, but I don’t think it’s such a bad move for him to be on Match.  I advised him to use this opportunity on Match to just meet people.  Talk to them.  Don’t make any expectations.  If he’s not ready to be dating, to keep things very casual.  Use this time as practice.  Practice talking to new women.  Practice flirting with new women.  Eventually when he’s ready, he’ll have honed up on his skills.  I’m not interested in trying to fill the shoes of this man’s deceased wife, but I am open to being his friend.

This very cute guy who I was emailing with, but then because I am trying to be more bold, I asked if he wanted to get together sometime and nothing.  Maybe he’s slow in responding, lord knows I am.  I still have yet to respond to a handful of *matches*.  Or he just doesn’t want to meet me.  Whatevs, it’s his choice, just like I choose not to respond to some as well.

That’s it so far.  There are those guys that I need to either email or respond somehow to their winks.  I am finding it a bit exhausting trying to keep up with it all, now that I am actually giving it a viable shot and not just doing it half-assed.  I have a hard enough time keeping tabs my own life and those of my friends and family, never mind all of these guys I barely know.  I need a vacation.


  1. firecracker3

    My first reaction to the widower is ewwww and gasp. Only April?!?! He needs time to heal, therapy and family support not to be on any dating site for any reason. If he needs grief support there are sites and groups for that. Just my opinion though 🙂

    • Oh, I definitely don’t think he’s ready to date. But I don’t see the harm in him meeting and talking to others, especially if it’s kept casual (I’m not talking sex though). And he doesn’t hide it and is very open and forthcoming about it, it’s in his profile, so women he meets thru Match know his situation from the get-go. From what I could gather from our conversation, his wife’s passing was expected for awhile, so it wasn’t something that came out of the blue. He might have had time to prepare to deal with the grief. When my aunt passed, and my grandfather too, it was expected because they were so sick for so long. Our family had the time to mentally prepare for it. It doesn’t lessen the hurt, but it makes it a bit easier to accept and move forward.

  2. Congrats on the multiple dates! Very exciting!!

    I’ve seen that widower guy on Match, or was it Fast Cupid? I think he’s on both. Anyway, although I thought he was handsome, I kind of figured that he didn’t seem to be quite ready to be out there… that’s nice of you to talk to him though.

    • Thanks! We’re probably dating some of the same guys! Haha. At the very least, we’re coming across the same ones. We probably need to clue each other in on the really bad ones.

  3. Wow that’s a lot of prospects! I don’t know you can keep up with them. I was starting to lose track, before thing started getting serious with Chef. I mean within two weeks, I had Unbelievably Hot Guy, Single Ryan, POF Matt (never mentioned him on the blog), Chef, Break Guy, Farmer… too much! I was exhausted. I think we girls need to pace ourselves 🙂

  4. I am impressed! You are making the rounds and have a great attitude. Maybe you’ve inspired me to try Match. Maybe. Still thinking about it. Still hurt and angry from the past but this being lonely thing SUCKS. Maybe I’ll try Match. Maybe.

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