So Far, Age Ain't Nothin' But a Number

The dating an older man updates as promised.

Positives to dating a man in his mid-30s:

• He offers to pick me up instead of making me take the T to meet him somewhere.
  
• He opens the car door for me. And every door. And pulls out my chair in restaurants. Wow.
  
• He takes me out for really nice dinners. And enjoys really good food. And isn't afraid to try new things.
  
• Good in bed would be an understatement.
  
• He has an extremely amazing body. As in, better than most 25 year old guys I've seen.
  

Negatives:

• It's possible that he parties a bit much for someone his age. I haven't really seen it but it seems as though he goes out a lot and gets restless easily just sitting around. But then he is a bachelor living in Boston so what is he really supposed to do?

Other than that, I have yet to really find any negatives, except that he'll be 40 in 4 years, which scares the hell out of me. And he has shampoo for thinning hair in his shower

All talk of age aside, I actually really like the guy. He's cute (well, I think he's h-o-t) and fun and we've been having a good time together.

And so, the saga will continue. I thought this would die out a lot faster than it seems to be, so I'm just going to continue to enjoy it. And him. And his body.

*Lily*

Be Nice or Be a Biotch?

Suppose you're on a date, and you've figured out pretty quickly (or maybe even not that quickly) that it's not going anywhere. Not that you're not having a good time, or the person isn't fun, nice, or cool... you just know there are differences that would not result in a second date.

I've been in this position twice recently. With both men, I had a great time. We went out, ate, drank, and enjoyed good conversation. However, about halfway through the dates, I knew I had no interest in going out on a second date. My question is, should I be nice and have fun, or turn into a bitch to avoid any awkward "follow-up" calls? Maybe I should just set it straight at the end of the date, when we part our own ways? This is difficult, because I am a genuinely nice person, and if I'm having a fun time, I'm going to show it. However, I've always had problems with men in my life (even generally speaking) confusing my niceness for being "sexually/relationship-wise" interested in them.

What to do?

*Ashley*

Dating an Older Man- Asking For Trouble?

Age ain't nothin' but a number, right? So says Aaliyah anyway. But is she right? In my opinion, absolutely not. Age is way more than a number; it's the number of years you've been alive on this planet. And I think that must mean something. But does it mean enough to stop me from dating an older man?

For some strange reason, Ashley and I are constantly hit on by older men. I recently met one that I actually might kind of like. The problem? He's almost 11 years older than me. So what, you might say. So, I say, what the hell is wrong with him that he's still single? Harsh, I know, but really? You're hot, have a great sense of humor, seem to have some serious dough and a beautiful apartment. Clearly something must be off for you to be 36 and single. And just how long is it going to take for me to find that something out?

Because it is a belief of mine that lists solve everything, I've been forced to come up with a list of pros and cons to dating older men and I will now present them to you:

Why older men can potentially rock my world:

• They're over a lot of the issues 20-something guys seem to have (20-something boys are all so confused and lost)
• They have a stable job and money (hey, it doesn't hurt)
• They're over the partying lifestyle but still know how to have a good time (hopefully)
• They know what they're looking for in a relationship
• They're ready to settle down (also, see below)

Why I should stay far, far away from older men:

• They're ready to settle down (also, see above)
• There must be a reason they're still single
• They're probably afraid of commitment and have way too much experience being smooth
• They will age a lot faster than you and may slow down far before you're ready
• They grew up in a different generation and there way be too much of a gap. Can I really date someone who doesn't know what it's like to be a child of the 80s??

Clearly my list didn't solve a thing seeing as I'm still deeply confused as to why this fine specimen of a man is still single. In any event, I did agree to go on another date with him and will continue to write any developments. And when I figure out what is wrong with him, you will be the first to know.

Because I'm about 98% sure there is something wrong with him. But until then, I'll just enjoy his hotness.

*Lily*

Google- Friend or Foe?

For me, Googling isn't a question. It's inevitable. As soon as I meet a prospect, I Google them. Weird? Stalkerish? Possibly. But whatever is on the Internet is public information and isn't going to be kept hidden. This means that whatever, and I mean, WHATEVER I come across, definitely helps me form a conclusion whether I should go on a date with a person, if they are dateable, or even if they are "boyfriend" material, etc.

Patrick warned me on our first date that he had some "questionable" material on the Internet. He was a part time journalist and often wrote about dating, sex, drugs and alcohol, and typical guy randomness. When I found the 100+ articles online for myself, I proceeded to read every single one of them, mouth wide open, and occasionally forwarded/IMed the juiciest ones to Lily and others. While it was entertaining, I really didn't want to hear about what he thought of fake boobs. Or women hitting on him. "Whatever", I thought. We all laughed about it. Now, I think this could have been one of the first signs he was a freak!

Lily and I went on a double date a few nights ago (to be written about later), and of course, we both Googled our prospects. Nothing juicy came of hers, although I'm still questioning her keywork and quotation-mark skills. However, I found quiiiiite a bit of information on my prospect. Without going into specifics, there was no doubt in my mind, even before our first date, that this was going nowhere. After reading quite a few pages, articles, and reviews, I basically learned his age, family history, all about his job, and general life of the past 15 years. It's difficult, because one should keep an open mind when going into a situation, or developing any type of relationship with someone new.

My only advice is this. Be careful of what you put on the Internet. Always remember that this is public, and anyone (even your mom, dad, employer, and yes... your potential date) can read it.

*Ashley*

Post Office Square... or Pickup Park?

I love Post Office Square: ample number of benches in the shade and sun, live music, clean, beautiful fountain, blooming flowers, well maintained, and in close proximity to Dunkin Donuts (yes, this does matter!). It's a great place to read a book, enjoy the beautiful weather, or people watch... all without the sketchiness of Boston Common.

Until last week, I went to Post Office Square assuming that the majority of people were "looking for the same things" when going to Post Office Square. This was until I was browsing on Yelp and saw Post Office Square refereed to as Pickup Park. "WHAT?!", I thought to myself. "My park is not a place to scout out potential dates!". However, the more I thought of it, the more it made sense, and the more I decided it COULD favorable place to meet a potential mate. There would be no beer goggles or fuzzy alcohol induced memories, nor would have you have tell people you "met at a bar". Plus, it's a given that the majority of people there during lunch hour have good jobs, are self sufficient, and live in or around the Boston area.

Then, a few days ago while reading the Missed Connections on Craigslist (yes, I do this), I found a Missed Connection for "all the women in Post Office Square" from a man saying how me "loves seeing young women dressed in business clothes and high heels" and thanking them for making his lunch more pleasurable. Sadly, this Missed Connection was not directed towards me, as I frequent Post Office Square in yoga pants and sun dresses. But again, hearing about Post Office Square being such a pickup place surprised me.

Then it happened. While minding my own business and reading a book during lunch hour at Post Office Square, a good looking man sat next to me and began talking. And talking and talking and talking. Finally, after an hour, it was time for me to leave, he asked for my number and said at the very least, we could go to a restaurant we both frequent. It would have been easy enough to say "Well, it was nice meeting you. Have a great day!", but that's not how it ended. I was picked up in Pickup Park! WTF?! He seemed nice enough, and would be an enjoyable date, but I couldn't believe that this place I loved simply for a nice place to read a book was proving itself as the pickup joint it was written about online.

And I'll probably be back tomorrow!

*Ashley*

You're Not Getting Ass But You Want To Pay? OK!

Nothing can really make one feel better after a breakup. The days and weeks following such a traumatic event in ones life can seem pretty bleak. Can't stop crying. Can't eat. Everything you see reminds of you of your ex-significant other.

After about two weeks of sitting in my apartment, crying my eyes out, losing a good amount of weight from not eating, and reading an array of self-help books, I decided it was time for me to stop feeling so sorry about myself. This was HIS loss and MY gain. I was only one step closer to finding the person I am supposed to be with for the rest of my life. Riding the wave of sudden optimism, I showered, got somewhat presentable, and trotted my way down to one of my favorite restaurants on Newbury Street. Certainly, my favorite restaurant and favorite food would make me feel better, right? With my People Magazine in hand, I was looking forward to chilling at the bar and enjoying the company of myself.

Oops. That didn't last long. Did I look like a vulnerable target? Was I asking to get hit on? Certainly not. However, shortly after ordering a drink and one of my favorite comfort food lunches, two 45ish year old men sat next to me. Granted, it was 1PM on a Saturday, but this did not matter to them. They were already hammered. Talking amongst themselves, I overheard their plans of a "guys night". Finally, my lunch arrived, which apparently signaled the OK to start talking to me. I really didn't feel like talking to anyone, especially two unattractive, middle aged men; however, I played along and made small talk. In all of about 15 minutes, I learned where these men work, live, how many woman they are dating (double digits, people... may have been a lie), previous stints in rehab, their preference in clothing and jewelry, and other random facts. They offered to buy me a drink, which I respectfully declined. They then asked me to join them on their drinking tour of the city, which I respectfully declined again. This disappointed them. These men weren't going to have sex with me.

However, I was quite surprised when I requested my bill, and the men said to the bartender "I've got it. I'm paying her bill."

Wait! I rarely accept free drinks from anyone, but they want to pay for my drinks AND my food? Even after I've made it quite clear that they aren't having sex with me? Score! I politely thanked them and left. No exchange of phone numbers. No promise to see them again. They were graced with the presence of my company for twenty minutes. And for that, I earned a free meal.

*Ashley*

Staying Friends

Note: Just to make everything a little easier, I'm going to call my Ex "Patrick".

One thing I was always thankful for was how much I got along with my Patrick's friends. In particular, his closest friends who live in Boston. They have liked me since Day One, have always been super nice, and told Patrick how fond they were of me and how lucky he was to have a girl like me. This seems quite uncommon, as many times, girlfriends see boyfriend's friends as threats, and vica versa. On quite a few occasions (as strange as it may seem), Patrick's friends and I got together without him around. Whether it was because coincidentally his best friend lived very close to me, or Patrick backed out of a commitment where we were all to hang out, I developed a bond between the two of them; a friendship that really had nothing to do with Patrick.

So, when he and I broke up, I was nervous. I really liked his friends, but was it OK for me to still be friends with them? Would they be OK being friends with me? And, if I were to remain friends with them, would it be difficult... like, would it be a setback to me? Funny, because within no time, they were both texting/calling/IMing me, wanting to hang out. While my friends, well... they'd want nothing to do with Patrick.

The three of us went out to watch the Celtics game a few nights ago, and to be quite honest, it was great. While- YES... it was a little strange hanging out with them without Patrick, we spent the entire night watching the Celtics, talking about life, and frankly- me venting about Patrick. Perhaps that wasn't the best thing for me to have done, but they were seriously understanding, supportive, and able to shed light on the entire situation. A good light, that only reiterated that I've made the right decision.

I'm quite sure that they aren't going to tell Patrick that we didn't hang out. As bad as it sounds, I wish they would tell him! He'd only realize what he so badly messed up.

*Ashley*