Stef Woods

Nothing says a first date like The Port Authority

I went on Match.com for a few weeks last March. Some of my friends in NYC had been using the site, and I thought it would be a fun diversion from Lawyer Boy. If you’ve read my entries about Brooklyn Boy, you know that one match was a bust. Mr. Port Authority is the other guy I met through the site.

From his profile, Mr. Port Authority was totally my type. He looked so much like my ex-boyfriend, Matt, that it was almost freaky. He also loved sports and was preparing to start his surgical residency. (My hospital stories are almost as entertaining as my dating stories so I tend to hit it off with people in the medical profession.)

We spoke several times over the phone, and I was preparing to see him when I got back to DC. In our last call, he asked me to leave NYC early or go back to DC for just a night, which I viewed as illogical and too eager. I don’t understand guys who get so clingy before we’ve even set eyes on each other.

I tried to look past this yellow flag since I was interested in meeting him. Two days later, I was at the hair salon in NYC, when I got a text from him:

“I’m in NYC for the day! Want to get together?”

We started texting back and forth, and he said that he was in the City to drop some info off at hospitals and to try to see me. Hmm….the Cling-O-Meter is rising and that’s not a good thing.

I knew enough about the residency match process to know that the results were coming out in a week. This guy is clearly not Type A or anything close to that if he waits to speak with hospitals until the 11th hour. His stock is falling since I’m far too motivated to deal with someone who isn’t at least a Type B.

I asked him where he was and he threw out an address that was THREE blocks from my family’s apartment in NYC. I exhaled and tried to convince myself that this was just a coincidence. I don’t remember if I told him where in NYC my family lived, but it was a tad creepy.

“Where were you thinking of meeting up?” I texted.

“What if we meet at The Port Authority for a hug and coffee before my bus leaves?”

The Port Authority? Who wants to meet someone for the first time at The Port Authority? That building is just one notch above a sewage treatment plant. My friend, Amy, summed it up perfectly when she said, “Does he want to kidnap you and take you to New Jersey?”

I decided to pass on this tempting offer [insert sarcastic eye roll here] and suggested that we wait to meet until we were both back in DC. By this point, my friends thought he was a stalker. I thought he was needy and socially-awkward. Regardless, Mr. Port Authority was making Mr. Starbucks look good, and that’s not saying much.

Purple Thong Boy

This is an oldie (a dating adventure from 2002), but a goodie.

I met Michael at Cheesecake Factory on a Saturday morning. That should have be enough of a sign that he wasn't going to be my Prince Charming. But, he was tall and very attractive with light black skin and a Georgetown degree so I gave him my number.

We would meet for drinks now and then. It wasn't serious (no love and no sex), but he was fun to hook up with. Michael always seemed to travel with at least one — and often, several — of his boys. I would get calls from his best friend, Charles, and some nights, both of them stayed over at my place. Back then, I was living in a studio and just had a bed and no couch so sleepovers at my place were quite cozy. But, Charles was always very respectful and Michael was amusing so it wasn't a problem.

On one particular day, I was at work and got a call from Michael. He and his friend, Dylan, wanted to take me out to lunch. I rolled up to the bar at Friday's and found them both already buzzed at 1pm. This Friday's doesn't get much traffic during the day so I felt really bad for all the senior citizens having lunch there. Michael was all over me like it was 3am and we were leaving a club.

He then started talking to Dylan about how much he liked kissing me and wouldn't Dylan like to kiss me. Dylan seemed open to it, and I replied, "Sorry. I'm not MCI. I don't do Friends-and-Family." (An MCI reference is dated, I know, but those ads were all over TV back then.)

I had to head back to the office, but Michael and Dylan mentioned that they might come over later and we could go out to dinner. I just told them to give me a call. Several hours later, as I got home from the gym, my phone rang. It was Dylan, saying that he and Michael were coming by with Chinese food in an hour. I told him that I was pretty beat, but if it was just for a few hours, that was cool.

Shortly after the call, Dylan showed up at my door with a bottle of wine.

"Where's Michael?" I asked.

"He went to get the Chinese food. He should be over in a little."

An hour later, I was starving and Michael still wasn't here. Dylan left a message for Michael, but he didn't call back. By this point, the wine bottle was almost empty and I hadn't had a glass. As Dylan got more and more buzzed, he kept moving closer and closer to me. Then, he offered to give me a foot massage. Umm…no thanks.

Finally, I just said, "Is Michael really coming over?"

"Well, I think so. But, you know him. He's probably out with another girl."

"We're not in an exclusive relationship," I replied. "He's free to date whomever he chooses, as am I. I just don't feel comfortable having you over if he's not coming."

"Oh. Okay. Can I just use your bathroom?"

"Sure," I said.

I kept watching the movie and was trying not to fall asleep. But then, I noticed something out of the corner of my eye. Dylan came out of the bathroom, wearing nothing but a lavender thong. What kind of guy wears a LAVENDER THONG? (Most guys I know wouldn't be caught dead in a thong — ever.)

I tried to look away because it was like watching a train wreck. He then started prancing around in the thong, jiggling his package. "You want some of this?" he asked.

"NOOOOO! Put some clothes on and get out of my place."

"Don't you like me? I know that I could satisfy you. Michael said that you were really fun."

"Get the hell out of my place! NOW!"

He put on his clothes and left. The image of him in the thong still haunts (or amuses?) me to this day. It was so wrong that it was funny. No guy should be wearing a thong unless he's a professional bodybuilder. And, Dylan was definitely not that.

A few days later, Michael called and I told him what happened. He had absolutely no idea that Dylan had even come over to my place, let alone under false pretenses. When I told him the purple thong portion of the program, he was livid. Michael and Dylan worked for Michael's father's company. Dylan lost his job because of this since Michael and his dad thought this was so irresponsible.

Even though I only spent a few hours with Dylan, I will never forget him. Thank you for the laughs, Purple Thong Boy!

Happy New Year's everyone!

Brooklyn Boy — Part II or What Not to Say on a Date

I was really looking forward to my date with Brooklyn Boy and saw the evening as a chance for us to get to know each other better. We went to a nice lounge in Chelsea and a casual, Asian-fusion restaurant in Union Square. I’m not one who requires a guy to be overly chivalrous or attentive, but I do notice those things. I offered to pay my way at the lounge and at dinner, and he took me up on both of those offers.

That might have made more sense had he not gone on – almost ad-nauseam – about how he’s trying to figure out how this relationship can work if we live in different cities the majority of the time. (Hmm…I didn’t know we were in a relationship yet.) I said that we would see each other over inauguration, which wasn’t too far off. He replied that a month was a very long time to wait. Seriously? We don’t even really know each other. Does he want me to run in the opposite direction? (That tends to happen if someone gets super-clingy with me after only a few dates.)

The night got worse when he tried to kiss me. Much like I did on our first date, I told him that I wanted to take things slowly and didn’t want him to be the rebound guy. He then started negotiating like we were 15, and he was trying to get me to have sex with him for the first time:

“Just a little kiss. It’s not a big deal.” It is to me.

“A kiss isn’t taking things quickly.” At our age, a kiss rarely stays at just a kiss for very long. Plus, isn’t the physical connection the easy part? It’s much tougher to find someone with whom I connect emotionally and intellectually.

“Do you not believe in PDA?” Yes, if I’m comfortable with someone.

“Relationships are about compromise.” But we aren’t in a relationship yet…

“Are you a prude?” I tried not to laugh out loud at this. The boy has no idea what I freak I can be…with the right person.

The prude comment really made me feel like I was 15 again. It got worse when he cornered me outside of the bathroom on our way out of the restaurant and kissed me. He didn’t ask if that was okay. He just did it. I went along somewhat reluctantly.

The seven-second kiss was one of the worst kisses of my life. Brooklyn Boy kisses with the FLAT part of his tongue. He doesn’t use the tip of his tongue. He doesn’t maneuver the flat part of his tongue gently. He just came at me like a hyperactive dog. Ugh!

To make the evening even more bizarre, Brooklyn Boy relayed a Woody Allen joke to me… about rape. If you care, read the section about Harlene Rosen here. Rape is never funny. After he saw my reaction and I emphatically stated, “That’s not funny,” he apologized. I accepted his apology, but it just didn’t seem sincere. I felt like he really didn’t get how inappropriate it was to relay that story. Period.

I ended the night, thinking that I might see Brooklyn Boy again. (I know. I need to make better guy choices.) But, after sleeping on the prude question and rape joke, I realized that I don’t care to see him again. I don’t know if he doesn’t respect women or just doesn’t get them, but either is a deal breaker for me.

He contacted me this week, and I wrote back an e-mail that I just didn’t feel comfortable with some of the comments that were made and wished him the best in 2009. He then asked me to tell him what he said. I kept my response brief (asking me if I was a prude because I didn’t want to kiss you and telling the Woody Allen rape joke made me feel uncomfortable), and he wrote the following:

“Boy was I misunderstood. The Woody Allen joke was something I had heard and wasn’t my invention. I thought I had put forth the disclaimer and apology once you stated that you worked with abused women. I know it’s a serious matter…Please contact me again. Go with what you felt when you talked to me not what you added to the event which took place in your memory. I really do like you and would like to see you again.”

Wow! So, if you didn’t come up with the joke and apologize afterwards, that makes it OK? And, I had to try not to laugh that he’s making it sound like he’s misunderstood and that my memory is faulty.

I actually don’t disagree with his take on what was said, but I don’t care to engage him further. He clearly doesn’t get that it was wrong to relay the joke at all. I sent him a one-liner asking him to respect that I don’t care to communicate further to which he wrote me back another long paragraph. I’m not replying anymore. How much do I have to say to a guy who made me buy my own dinner, thought it was acceptable to tell a joke about rape, and kissed me with a flat tongue when I didn’t even want to be kissed :p?

Brooklyn Boy — Part I

I recently ended a relationship with a man I loved…a lot. I know that it was the right decision to break it off with him, but it still hurts.

I'm not a serial monogamist and know that I'm not ready to be in another relationship anytime soon. But, I still enjoy dating and going out for drinks with guys. So, I gave this Brooklyn Boy a chance.

He and I met earlier this year for coffee when I was wondering if I was ready to start dating other people. (I wasn't, as I was far too in love with Lawyer Boy, but I tried.) If I close my eyes and imagine the perfect guy for me physically, Brooklyn Boy fits the bill. Think 6'2" tall, dark and handsome with an athletic build. Brooklyn Boy's inside is as appealing as his outside. He's motivated professionally and well rounded with a love of traveling, foreign languages and sports. I like being able to talk politics with someone one minute and NCAA basketball the next. The fact that he spoke quite a bit about his family and how close they all are increased the value of his portfolio for me. Meeting someone for a quick coffee usually doesn't leave me wanting more. With Brooklyn Boy, it did.

So, now that I am officially single, I decided to e-mail Brooklyn Boy. He was game for getting together for drinks at a bar in Gramercy. The bar was modern, yet romantic, with dimmed lighting, lots of candles and velvet couches. On a Monday night, it wasn't too crowded for us to hear each other. The more we talked, the more I wanted to talk more.

He asked me when I was last in a relationship. I was honest with him and said that I recently ended something serious. I commented that I hoped he and I could keep getting to know each other and see what happens. Brooklyn Boy seemed fine with that…or so I thought. We were just sitting there on the couch, and out of nowhere, he tries to kiss me. Not a little peck, but a full-on open-mouth kiss. We haven't even spent more than three hours together cumulatively, and he's acting like we're at a frat party! (20-something City Girl would have been open to that, but 30-something City Girl is not.) I was totally caught off guard, but managed to steer the kiss to just a peck on the mouth. Thankfully, he didn't push it. We ended the night with another peck and agreed to see each other next week.

Was it naive of me to think that he wouldn't push it on our next date? Maybe. But, I was looking forward to spending more time with Brooklyn Boy and could not have foreseen just how bizarre that date would be.

A horrible first date

It was fall of 2007, when a friend IM-ed me about fixing me up with this guy he had just met. I’m not one for blind dates, but I was told that he was funny, attractive, educated and second-in-command at the embassy.

“Which embassy?” you might be asking.

Well, I probably shouldn’t say, but I viewed the embassy connection as a huge plus since I had lived in his country for a year. I was looking forward to the guy’s call and saw some potential. Boy, was I wrong! Read on to find out why our first date was also our last:

1. He picked Starbucks as the meeting place (Picking Starbucks is not a deal breaker on its own, especially for a casual and quick get together, but it’s definitely not the most creative place for a first date);
2. He asked when I was available. I said, “11.” And for the next 15 minutes on the phone, he kept insisting that we were meeting at 10. The following morning, he tried to get me to agree to 10:30. 11. I told him that it was fine if he wanted to grab breakfast on his own, but he insisted that he could wait until 11;
3. I rolled up to the Starbucks and noticed that he was already having coffee and a muffin with his roommate. Huh? He did not apologize nor did he introduce us;
4. He did not offer to pay (I’m cool with paying my way, but an offer is nice);
5. He maligned my choice in beverage from Starbucks as unhealthy. Since he’s neither my Mom nor my husband, I was not cool with that;
6. He then asked if I would drive him to the bank so he could cash a check. Who does their banking on a first date? I decided not to tell him what I really thought of him at this point and ride it out because we have a friend-in-common;
7. He got annoyed when I did not know where the nearest branch of his bank was located;
8. Next, he asked me to take him shopping since he needed things for his new place;
9. He became cross when I turned left, instead of right, to get to the store, despite the fact that I learned to drive in this city and know where I’m going, whereas he just moved here and doesn’t have a car;
10. He then asked me to take him to another place to drop off the items he purchased at the store;
11. He was wearing a fanny pack. (Initially he carried it over his shoulder, but then he put it around his waist — and kept it there);
12. He did not stop talking about himself and his pedigree. “I fence. I ride horses. I drink only the finest Italian wines. I have a flat in London;” and
Unlucky 13. After our “date,” he was deluded enough to call a mutual friend to say how much he likes me and express his confusion as to what went wrong?!? Are you kidding me? He doesn’t need a girl. He needs a driver and a personal assistant!

Mr. Starbucks, as I refer to him now, called me twice after this “date.” I, of course, let his calls go to voicemail. In his messages, he asked me to call him and mentioned us getting together again. I pressed delete. Can you blame me?

Is there a Puma inside of this City Girl?

I traditionally don’t date younger men. It’s not a rule that I have, but more of a preference. Someone my age or a few years older tends to be a better match for me personally and more relatable professionally. So, imagine my surprise when I was asked out by a guy who graduated high school the same year that I graduated law school. I’ve heard the term, “Puma,” used to describe a woman in her 30s who is dating a guy in his 20s. But, is there a Puma inside of this City Girl?

A few friends told me to “Go For It!” If Cameron Diaz and Drew Barrymore can do it, it has to be en vogue, right? I’ve gone out on a dates with guys who are 8-10 years younger than me, but have never seriously dated anyone that young. A 20-something guy can be full of energy under the sheets, but what happens when the initial cute factor wears off? I need a man to challenge and inspire me, not a boy looking for direction in his life.

Signs that I might not even care to grab a drink with this particular guy:

1. He asked which school I went to, and I responded with a well-respected women’s college. To which he replied, “That’s a smart school.” Umm…yeah. I didn’t even think he could handle the information that I was a lawyer and back in school to complete a third degree so I kept that information to myself;

2. He brought up the fact that I am in my prime at 35. (The two guys in their 20s who I dated in the past were also very-focused on this, too.) I’m all for research and statistics, but I’d like to think that women get better and better with age. 35 is my prime for now, but I bet I’ll be even more in my prime (sexually and otherwise) at 45;

3. He wanted to meet me at a bar…at 11pm…while he was with his buddies. I realize that all dates don’t need to be romantic or expensive, but I’m more of a one-on-one date kind of girl. I’m also used to coming home at 11pm, not going out at that hour; and

4. He asked if I was single and ready to mingle. Seriously.

I’ve been told that I have an aggressive personality with guys. However, I don’t think I’ll be “Roarrring” with a younger guy anytime soon. This City Girl needs a guy with Ferragamo or Prada loafers on his feet, not Puma sneakers, to bring out the Tigress in her.