Dating Support Network

This is a follow-up to the original post Long-Distance Cougar Dating. Sounds Made Up. There really wasn’t supposed to be a follow-up, but alas there has been an actual face-to-face encounter between our girl and boy. And there’s a new wrinkle in the story. So now we have no choice but to have a “Part 2.”

First it must be said that it’s not entirely clear if this encounter was an actual date. Boy came in from out of town and asked our ‘experienced’ (ahem) girl to meet him for a coffee (evidently they love coffee). They spent their time talking and laughing as if they’d known each other for years (more years than he had even been alive!). The conversation took many twists and turns, dipping slightly serious territory at times, but all without skipping a beat. There were even some innocent accidental brushes and then some intentional touching (get your mind out of the gutter – it was arm around the shoulder chivalrous stuff). It was effortless. It was natural. And for our jaded girl, it was refreshing.

Which brings us back to our tragedy. He’s handsome. He’s smart. He’s confident. And to make matters worse, she now finds out that he’s moving to her city! No more long distance! Only cougar (which is a term we despise if we haven’t said it before)! It’s like the universe is playing a heartless joke after all those years of putting in hard time on the New York City dating beat. “Now?” she cries, “You send this to me now?!”

So, DSN, our girl is confused. She enjoys boy’s company so much and briefly fantasizes about the ever-so-slim possibility that anything like this could work out in real life. But then she quickly snaps herself back to reality, shields her heart with her head, and reminds herself that a little old thing like fourteen years separates them.  She’s not sure she can do the actual cougar thing (i.e., just have ‘fun’), but thinks maybe it’s better than nothing? Get to typing people! Should she even entertain the idea of going there?

We normally don’t tackle celebrities in our “DATE or DUMP?” features, but the Sandra Bullock/Jesse James story is just too unbelievable to pass over. Don’t let the title of this post sway your vote (we think you can guess how we feel about it). Should Sandra find it in her heart to forgive, or should she kick his awful tattooed ass to the curb? Just this one time we’re actually adding a third option to shoot.

It’s time for another DATE OR DUMP! Readers submit their wooing woes and we ask you, the (lovely and talented!)Dating Support Network, to tell them what to do: Date? or Dump? Today: Is her boyfriend up to no good with his ex? Sinking Suspicion writes:

I have been dating my boyfriend for over a year. We don’t live together mainly because of my traditional upbringing. I never wanted to live with anyone until after marriage. Everything has been going really well up until the last month. His ex-girlfriend, who he was with for four years, called him to say she’s sick and needed his help. I’ve had no problem with them being friends, but he’s been spending A LOT of time with her since she told him she was not doing well. I’ve told him how I feel about it and he told me I was just being insecure. He hasn’t reduced the amount of time he’s spending with her, and she’s already started to get better. I’m worried that he’s falling for her again.

Alright Dating Support Network, vote below and comment to tell your fellow-reader what she should do.

It’s time for another DATE OR DUMP! Readers submit their wooing woes and we ask you, the (lovely and talented!)Dating Support Network, to tell them what to do: Date? or Dump? Today: Are we exclusive? Mister Mistreated writes:

I’ve been living with my girlfriend for two years (I’m 28, she’s 24). I made the decision to move in together with the intention of asking her to marry me some day. I want to get married by the time I’m 30. But I found out five days ago that my girl has been cheating on me with someone she works with. I really am in love with her, but I’m incredibly hurt and angry. We’re trying to work through it, but every time I think about proposing to her I feel like a total fool. How can I stay with someone who isn’t loyal?

What say you DSN? Is this cheater deserving of a second chance? Vote below!

It’s time for another DATE OR DUMP! Readers submit their wooing woes and we ask you, the (lovely and talented!)Dating Support Network, to tell them what to do: Date? or Dump? Today: Are we exclusive? Heartbroken in Hoboken writes:

I met this guy online about two months ago (I’m 28, he’s 31). We’ve gone out on five dates, which have all been fantastic. He’s smart, successful, and always treats me like a gentleman. I think I’ve really started to fall for this guy. I took my online profile down last week an we slept together for the first time a few days ago. He called me the day after, which is always a relief. I thought he might be falling for me, too. But I just happened to see him on what looked like a date with another woman last night. I also checked the website and saw that he’s still active. I know it hasn’t been that long and we haven’t had any talk about being exclusive, but I feel completely heartbroken. I feel like I can’t trust him. Should I nip it in the bud and let him go?

Well DSN? Is he a cheater? Is she jumping to conclusions? Expecting too much, too soon? Vote Date or Dump below and share your comments on why this is or isn’t meant to be.

I have a friend, Paul, who is currently dating the most incompatible woman in the world for him. Strike that. Living with the most incompatible woman for two years. His friends, family and dog are all so confused. It’s like they are defying the laws of nature by being together. Snowing in the desert or Jay Leno coming up with an original funny joke. No one can wrap their heads around it.

Paul doesn’t like to talk about his relationship all that much, but when pressed about how this most unholy of unions could ever exist, he makes the puzzle even more difficult to solve. “She’s not the one,” he says. “She’s fun and easy. She just makes me happy.” That’s when the dog’s ears go up and he tilts his head like he heard a funny, high-pitched sound. Oh wait, that would be everyone screeching, “Whhhaaattt??”

Clearly Paul has many layers of his proverbial onion to unpeel if he is ever to understand why he’s living with a woman he does not love. Cutting to the chase, I think Paul is terrified of being alone. He’s like a nervous cat that reels back when it catches a glimpse of itself in the mirror. When Paul looks at himself in the looking glass, I wonder who he sees looking back. I wonder what is he so afraid of finding. Does he think he is not worthy of a true romantic partner who will love and challenge him? Is he ashamed of who he is for some reason and using his live-in easy lover as a shield, distracting him from taking a deeper look inside?

What Paul doesn’t understand is that by keeping this woman so close to the vest, he is doing himself a major disservice. Days will turn into weeks and into months and then years without him knowing who he really is, all because he feels like he doesn’t have to. He’s got someone who “makes him happy” and that’s all he needs. But when I look into his eyes and observe his body language, happy is not what I see. His avoidance of himself is sapping all of his energy. Sooner or later, it will catch up to him.

I have a challenge for you Mr. Paul. Find the courage to be on your own. Take some time to get to know yourself. You need to be solo to do this. No diversions, no silly games. You’re too old for those by the way. Once you are able to dig deep and let the real you emerge, you might just be surprised by who will come into your life.

What do you think about being alone vs. being with the wrong person DSN? Share your thoughts!

Okay, okay, I know Conan O’Brien is a happily married man, and the kind of support he needs right now is not in the dating realm, but I can’t help but send some love his way as he fights the most vicious battle of his professional life.

When I heard the news of how NBC was screwing him (and not in the way we here at the Dating Support Network would prefer), I at once felt a sense of indignation, defensiveness, anger, and even sadness. But as much as I like Conan O’Brien, I was very surprised by my strong emotional reaction. I’ve personally never met him, so why did I feel like marching up to the NBC executive suite to give all of those bozos a good finger wagging and talking to for hurting my Conando?

Then it dawned on me: Conan has been a constant in my late night routine for seventeen years. I repeat, SEVENTEEN YEARS. Every night I’ve tuned in to get a laugh, and he’s never let me down. He’s wickedly smart, genuinely principled, and boyishly cute. And it doesn’t hurt that he’s tall (sorry, boys, but girls like that). Now that’s the kind of guy I wouldn’t mind sharing my boudoir with.

So, I fully recognize and admit that I have had, still have, and will always have a thing in my heart for Conan O’Brien. And I’m not the only one. Megan Fox admitted just as much on her last Tonight Show visit. Gabourey Sidibe also told Conan that her best friend, Crystal, had a fantasy about Conan – involving Jello. I’ve never heard anyone say that about Jay Leno (ew).

Yes, Conan O’Brien, you are quite a catch. I don’t doubt that you’ll be back on the air somewhere sometime soon, and I’ll be watching from day one. And if your wife ever dumps you like NBC did, you know where to turn (to the DSN of course!).

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