Category: second dates


A Second Date With A Semi-Surprising Outcome

December 8th, 2012 — 7:40pm

My second date with Long Island bachelor and OkCupid member E began much like the first – at a fabulous nightspot in Chelsea.

We met for drinks at The Darby, an upscale jazz club and restaurant with rich, elegant décor and great music. As we clinked glasses, E said I looked pretty and we made easy small talk about the holidays and our plans for the evening.

For dinner, E chose Crispo, a first-class Italian bistro with a cozy main dining room featuring exposed brick, a waterfall and wrought iron chairs. The food was amazing – I had black truffle ricotta ravioli and we shared a sublime tiramisu for dessert. Along the way, E asked a lot of questions and listened intently as I told him about my travels to Australia over the years and what I learned during my U.S. Dating Blitz.

Crispo serves delicious, authentic Italian fare (Photo Courtesy: Whollygastromony.com)

I found myself thinking maybe I had read too much into his gay-related observations on date #1 — until we got to Canal Room down in Soho.

As we waited for awesome 80’s tribute band Jessie’s Girl to take the stage, E quoted some advice a friend had shared with him–

“’If you like this girl, don’t tell her you like Neil Diamond.’”

While I’m processing why he’s telling me this, E reflects on how popular tight jeans were during the 80’s – and gestures toward the rear end of a guy in front of us who’s wearing them.

At this point, I can’t ignore the fact that my gay-dar vibe is sounding an alarm. I try putting that aside once the concert starts, doing by best to just enjoy Jessie’s Girl’s energetic set of 80’s classics. But when E leans over – twice – to comment on the band’s muscle-shirt clad male backup singer, my patience begins to wear thin. Nothing’s a bigger buzzkill than having your date make eyes at other men.

E and I shared an awkward cab ride back uptown.

“I’ll talk to you soon,” he called out as he shut the door and I knew that wasn’t going to happen. Because clearly, he has a few things to figure out when it comes to who exactly he wants to date.

Though I managed to eventually find the humor in this unexpected episode, it also served as a cautionary tale of what can happen when you rely too heavily on the Internet to find love. I’ve said it many times and it bears repeating: online dating is a lot like gambling. There are the lucky few who hit the jackpot and then there’s everybody else. I, for one, have had my fill of cyberspace-instigated dates. So I’m officially taking my online profile down and making a New Year’s resolution to get offline and back out there again.

The quest for love continues.

| 80's cover band, Canal Room, Chelsea, new year's resolutions, OKCupid, online dating, second dates

Catching Up With A Dating Blitz Bachelor

September 16th, 2011 — 9:53pm

Last weekend, I enjoyed a long-awaited second date with the first bachelor from my European Dating Blitz, Ireland-born Pete.

In the year since we met in Dublin, Pete and I have kept in touch via Facebook, email and instant messaging. He even sent me a postcard from Paris, confirming my initial impression of him as one of the true good guys.

I broke out a brand new LBD for our date, a decision I was doubly glad about when I spotted him running across the street toward me. Clad in a gray suit and fedora, he looked even more handsome than I remembered him to be.

Luna Piena: Pete and I enjoyed a delicious dinner at this Midtown bistro

After a quick hug, Pete and I settled into an outdoor table at Midtown Italian bistro Luna Piena. Over dinner, we filled in the blanks about where our lives have taken us over the past 12 months, reflecting on career shifts and milestones both happy and sad (his recent 35th birthday, the 13th anniversary of my mom’s passing).

Pleasantly full from our respective entrees and shared profiteroles for dessert, we walked over to the Pod Hotel where Pete was staying. He led me up to the paved roof deck, for a glorious moonlit Gotham view of Midtown. As we took a seat so we could take it all in, Pete said–

“I think we should pledge to meet up like this every year.”

“I agree.”

Our last stop of the night was Sofia Wine Bar, for some cozy conversation about favorite bands — and when and where we might see each other again (a return to London is on my radar for early 2012). Pete walked me to a cab. We embraced, reiterating how happy we both were to have seen each other again.

As the taxi pulled away, I found myself marveling at the randomness of how we’d met (Pete reached out after reading about my Dating Blitz in a local newspaper). And feeling thankful all over again that geography is no match for a genuine connection.

| second dates, The European Dating Blitz, wine bars

A Long Delayed Second Date

March 1st, 2011 — 4:28pm

Cyberspace is a notorious breeding ground for what I like to call the dating equivalent of ADD. Initial connections often fizzle out quickly because of short attention spans — which is one of several reasons why I was so excited about date #2 with adorable Spaniard Inigo.

Inigo and I went out back in January after connecting on OkCupid.com. We had a great time, but then opposite schedules got in the way. He travels to North Carolina during the week for a consulting gig and I’ve been away for the last three weekends.

Still, Inigo remained in touch, calling and texting to find out when we might both be in the Big Apple again at the same time. Friday night, it finally happened.

Peep SoHo: Great Thai food in a funky (albeit kind of noisy) setting

We met up in SoHo, where our first stop was funky Thai bistro Peep for dinner. From there, it was off to drinks at cozy Thom Bar in the Thompson Hotel. Over cocktails, we talked about our recent travels, favorite spots in NYC (Central Park and The Cloisters among them) and upcoming movies we would like to see — possibly together.

As we shared a cab uptown at the end of the night, Inigo put his arm around me. I couldn’t help thinking that when you least expect it, welcome surprises do happen in the journey of dating. Here’s to many more of them, in and out of cyberspace.

| OKCupid, online dating, second dates, SoHo

Madrid: Day Four & Date #2

October 11th, 2010 — 5:28pm

On my last day in Madrid, I enjoyed a second date with adorable Spanish bachelor Victor, 32.

Taking advantage of the glorious summer weather, we had a round of drinks outside, talking about differences between sports in the US and Spain, and falling into the easy banter of our first date a few days before.

For a late afternoon lunch, we headed over to Mano A Mano — one of Victor’s favorites for paella. I had the gastronomic pleasure of discovering why as we shared a heavenly paella with lobster.

Lobster Paella at Mano A Mano: In a word, delicioso!

As we lingered over it and a bottle of wine, Victor said sweetly how much he had enjoyed spending time with me, a sentiment I echoed. He invited me to join him and a few friends at a bar to watch a Spanish soccer match.

Though it was fun witnessing first hand the fiery local passion for soccer (and hearing plenty of cursing en Español), I could feel the effect of six weeks of travel catching up with me. In other words, I was exhausted from making small talk with strangers.

Me At Retiro Park: Madrid’s main park is stunning

So, after kissing Victor — only on the cheek, unfortunately — goodbye, I made my way over to Madrid’s stunning Retiro Park. It seemed a fitting place to wind down the final day of my European Dating Blitz, taking in the local crowds at sunset and reflecting on where my journey had led me.

Much like the first blitz, I found myself thankful for the adventure and all that I had learned about what it’s like to be single outside of New York. Only this time, I was going home with a renewed appreciation for my hometown — and a readiness to take a little breather from dating.

Of course, like the cliché goes, it’s when you’re not looking that interesting people tend to cross your path. Coming up…the full scoop about unexpected flirting since I got home and a second encounter with one of the best bachelors from my first Dating Blitz!

| Madrid, second dates, The European Dating Blitz

Saturday Double Header

July 9th, 2010 — 5:01pm

Last weekend, I enjoyed an action-packed Saturday that began in Central Park with my friend Crystal.

Row Your Boat: Crystal took this picture of me in Central Park

Over a delicious brunch at the Loeb Boathouse, Crystal and I talked about the joys of redecorating and the frustrations of lackluster dates. When we rented a rowboat for an hour, I told Crystal how much more fun it was with her than with a dull date last summer.

Later, craving something cool, we walked over to the Godiva store on Madison Avenue and treated ourselves to a Chocoelixir drink with caramel. Beyond decadent and equally delicious. We were savoring the taste when I looked up and spotted this sign on a lamp post–

“Curb your calories, and Eat Less.”

I love New York — it always has a hilarious sense of timing.

That night, I headed down to NYC’s West Village for date #2 with White Plains bachelor and talent booker Paul. After a quick cocktail at a nearby wine bar, we went to see “Nunsense.” The long-running musical comedy serves up a lot of laughs and kitschy one-liners, so it was easy to understand why Paul has seen it three times over the years,

Over a delicious post-show dinner (gnocchi Bolognese) at Zucca Trattoria, Paul and I reflected on the differences between city and suburban life. I found myself wondering if I could really leave the concrete jungle of Manhattan behind someday. And feeling thankful that, for now, I’m in no immediate danger of having to make that choice.

| Central Park, second dates, West Village

Opening The Vault: Part Seventy

June 11th, 2010 — 5:00pm

When you truly connect with someone, it can overcome even the most mixed signals. Thankfully, that’s exactly what happened after my first date with Southern Illinois native Steve back in 2001.

Steve surprised me by ending a flirtatious, conversation-filled evening with a handshake. Our second date concluded very differently. I now Open The Vault and take you back to December of ’01…

December 20, 2001
New York, NY

Dear Diary,

I’m just amazed at how good the communication is between Steve and I. I’ve been without a man who stimulates all of me for so long, it’s still hard to believe what I’ve found with him.

For our second date, we drove to Carbondale again for dinner at Chicago Underground. The food was only passable, but our chemistry continued to grow. I felt truly at ease with Steve and loved hearing his stories and his laugh.

Unfortunately, like our meal, the movie (“Spy Game,” an espionage flick) was a disappointment — so much so that I fell asleep. My embarrassment turned to relief when I woke up and Steve suggested–

“Do you want to leave and go rent Dirty Dancing?”

Dirty Dancing: things heated up between Steve and I as we watched the memorable 80’s movie

We had discovered during dinner our mutual love for the classic 80’s movie, so I happily said yes.

At my place, Steve sat right next to me on the couch. I could feel my insides reacting to his proximity and loved every second of it.

I became increasingly distracted, finding it hard to concentrate on something other than Steve. Finally, the movie ended. We made some small talk, but I couldn’t hide my feelings any longer.

“Do you usually end your dates with a handshake?” I asked.

“No,” he said, smiling irresistibly. “And I did want to kiss you the other night.”

“Do you think you’re going to tonight?”

“I think I’m definitely going to.”

And with that, his lips came to mine.

“I want you so bad,” he murmured as he caressed my back.

The subject of getting together again came up.

“How about tomorrow?” he whispered in my ear.

Our goodnight kiss was wonderful. After Steve left, I was glowing. It’s been a very long time since I’ve felt this kind of connection with a man.

The question now — what comes next?

* * *

With my return to New York right around the corner, Steve and I quickly found ourselves in a long distance relationship, one that would be tested by an opportunity for me to live on the other side of the world.

| Dirty Dancing, long-distance relationships, Opening The Vault, second dates, Southern Illinois

An Exciting Second Date

November 25th, 2009 — 11:09pm
Friday night, I enjoyed an exciting second date with adorable 37-year-old PR executive E.

Bond 45: Great food and service in a bustling Theater District landmark
(photo courtesy: Shanna Ravindra, New York Magazine)

We met up at historic steak and seafood restaurant Bond 45. E took my face in his hand and greeted me with a quick kiss.

“You look great,” he said as he sat down. I smiled, grateful for the good hair day that I was having thanks to a quick blowout at lunchtime.

Over a delicious dinner (skirt steak cooked to perfection), E and I talked about our shared appreciation for architectural history and “NYPD Blue,” and our fondness for the good music and fun to be experienced at weddings.

Upon mentioning that I’ll be attending a friend’s nuptials in Boston next month, E asked if he could be my plus one. If only I had been invited with a guest.

After dinner, while walking through Times Square, E kissed me. I could feel every part of me ignite at his touch and, for a moment, I literally forgot where I was. Heaven.

E treated us to one of the most entertaining Broadway shows I’ve ever seen, “Burn The Floor.”

The high-energy two-hour ballroom dance extravaganza features stunning choreography, fantastic music and couples that truly sizzle. Anya and Pasha of “So You Think You Can Dance” were among the show’s talented troupe, which also boasts dancers from as far away as Russia and Australia.

Next, we headed downtown to E’s office on Hudson Street, where we took in sweeping city views from the roof deck — and shared a few kisses in the moonlight.

Over drinks at a nearby Irish pub, E leaned forward and pulled at the ribbon on my top, clearly not realizing it was purely decorative.

“You need level 3 clearance for that kind of access,” I teased, “Right now, you’re only at level 1.”

“That’s okay,” he responded with a smile. “I have a lot of patience and I’m not going anywhere.”

Our last stop of the night was a tiny eatery designed like an old ship, where we shared a few appetizers and talked about favorite TV shows and portable gadgets.

Later, E walked me to a cab and pulled me into another knee-weakening, lingering kiss.

When it comes to second dates, it simply doesn’t get any better than this.

| Bond 45, Burn The Floor, second dates, Times Square

An Exciting Second Date

November 25th, 2009 — 6:09pm
Friday night, I enjoyed an exciting second date with adorable 37-year-old PR executive E.

Bond 45: Great food and service in a bustling Theater District landmark
(photo courtesy: Shanna Ravindra, New York Magazine)

We met up at historic steak and seafood restaurant Bond 45. E took my face in his hand and greeted me with a quick kiss.

“You look great,” he said as he sat down. I smiled, grateful for the good hair day that I was having thanks to a quick blowout at lunchtime.

Over a delicious dinner (skirt steak cooked to perfection), E and I talked about our shared appreciation for architectural history and “NYPD Blue,” and our fondness for the good music and fun to be experienced at weddings.

Upon mentioning that I’ll be attending a friend’s nuptials in Boston next month, E asked if he could be my plus one. If only I had been invited with a guest.

After dinner, while walking through Times Square, E kissed me. I could feel every part of me ignite at his touch and, for a moment, I literally forgot where I was. Heaven.

E treated us to one of the most entertaining Broadway shows I’ve ever seen, “Burn The Floor.”

The high-energy two-hour ballroom dance extravaganza features stunning choreography, fantastic music and couples that truly sizzle. Anya and Pasha of “So You Think You Can Dance” were among the show’s talented troupe, which also boasts dancers from as far away as Russia and Australia.

Next, we headed downtown to E’s office on Hudson Street, where we took in sweeping city views from the roof deck — and shared a few kisses in the moonlight.

Over drinks at a nearby Irish pub, E leaned forward and pulled at the ribbon on my top, clearly not realizing it was purely decorative.

“You need level 3 clearance for that kind of access,” I teased, “Right now, you’re only at level 1.”

“That’s okay,” he responded with a smile. “I have a lot of patience and I’m not going anywhere.”

Our last stop of the night was a tiny eatery designed like an old ship, where we shared a few appetizers and talked about favorite TV shows and portable gadgets.

Later, E walked me to a cab and pulled me into another knee-weakening, lingering kiss.

When it comes to second dates, it simply doesn’t get any better than this.

| Bond 45, Burn The Floor, second dates, Times Square

An Eventful Week

November 21st, 2009 — 10:14pm

When it comes to the perfect mix of female bonding, nights out on the town and budding romance, this week had it all.

Girls Night Out: Heidi and me at The Lost Girls happy hour

From a happy hour celebrating The Lost Girls and their upcoming memoir and a schmoozefest at one of NYC’s hottest event spaces to an exhilarating second date with adorable HurryDater E, I’ve been on the go non-stop and enjoying every minute of it.

Coming up…details of all the action and the debut of a new SGITC feature.

| Girls Night Out, happy hour, second dates, The Lost Girls

An Eventful Week

November 21st, 2009 — 5:14pm

When it comes to the perfect mix of female bonding, nights out on the town and budding romance, this week had it all.

Girls Night Out: Heidi and me at The Lost Girls happy hour

From a happy hour celebrating The Lost Girls and their upcoming memoir and a schmoozefest at one of NYC’s hottest event spaces to an exhilarating second date with adorable HurryDater E, I’ve been on the go non-stop and enjoying every minute of it.

Coming up…details of all the action and the debut of a new SGITC feature.

| Girls Night Out, happy hour, second dates, The Lost Girls

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