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Wednesday, April 16, 2008

Official Decree

I am lifting the ban. This could be the perfect opportunity for a young man looking to get in on the ground floor with a smart, funny, sexy, independent, low-maintenance woman. Clearly, whatever issues I have surrounding dating, self-esteem is not one of them.



I do have some questions for my loyal readers. (assuming that I do have loyal readers. Hello! Is anybody there? The numbers on the tracker keep going up, but you know, the comments option is there for a reason.)

I think that the whole dating thing has changed since the last time I got into all that. So, first question.


  • How do I find guys to date? I work for a professional theatre company, so clearly, I'm not meeting any eligible guys through that avenue. Well, I am, just not eligible for me. I am meeting lots of fantastic men who are great dancers and have excellent fashion sense. Anyway, back to the topic at hand. I used to live in a hip little town, where meeting people was fantastically easy. But now it's not so easy in the big bad Boston. Everybody says that the internet is the way to go. Okay, I guess we actually did answer that question.

  • How does one plan a date? What should one do? And how does a person who doesn't drink deal with date jitters?
  • What's the deal with the whole sex on the third date thing? Is that a myth? It seems awfully regimented.
  • Okay, here's a really tough one. I've always had really close male friends. Where is the line between friendship and something more? The line between date and hanging out? How can you tell the difference between 'he's just not into you" and "he is into you but he's shy and/or respectful?" How do I let someone know I'm interested in them without being a total embarrassing dork? Can I just have a friend call his friend to find out if he likes me? Am I destined to be perpetually stuck in junior high?
  • At what point in the dating process do you tell someone your secrets? I don't have any dark, scary secrets, but there are some things you don't share right away. But, there are some things that you don't want to wait too long to tell.
  • Why am I doing this? Why don't I just go back to the plan of being a crazy cat lady? Oh, right. There are some things feline companionship just can't offer.

So, seriously. Leave some pithy advice. Use the comments. And if your best friend thinks I'm cute, tell my best friend and we can go roller-skating. My mom can drop us off if his mom picks us up.

7 comments:

leninwearsredsox said...

Obviously you most definitely need to take up another drug habit to deal with the pre-date jitters...although might I suggest a depressant of some kind, i dont think cocaine does a very good job of alleviating jitters. that is really all i have to say. i dont date so i dont have much advice.

bostonbear916 said...

well being one of those men you have met that can dance (well kinda) but i DO have great fashion sense(it is just too expensive to change my wardrobe on a weekly basis) i don't know if i can give you an advise...hell i can't even find my own man and can't figure out "if he likes me like i like him" like i told Matt "men are assholes and you can't live with them and you can't live without them"

Anonymous said...

Ok. I have to itemize my commentary.
-You covered the meeting people thing, but doesn't it still seem, well, odd to you? Theoretically, a "big bad" would have a lot more to offer in the way of attractive, smart, eligible males in the appropriate age group. Or do they all spend so much time sitting on their computers like we do, leaving young, attractive, intelligent women with no other options?
-Date planning. As a recently single woman, I understand that this is an excruciating process. So you look at the various profiles, piece together some common interests, and hopefully manage to make it interesting and/or not awkward. I had a friend who used to say "never eat on the first date", as if men would be somehow reviled by a woman who enjoys food, but it's perfect. You always have an excuse when the conversation isn't quite as sparkling as you had hoped. If it takees a long time to finish your meal, that should be a sign. Who couldn't stop talking?
-Date jitters: carbohydrates and cheese. Tryptophan slows everything down, feeling drowsy is better than freaking out. As long as he doesn't think you're bored. You could always use the "it just means I am very comfortable with you", which hopefully would be true.
-Sex on the third date. Never heard of it. Don't care. Let someone else worry about those ridiculous myths, work within your own parameters.
-As far as close male friends go, I've had the same issue with some of mine. Here it is: guys are not terribly mysterious creatures, unless they work really hard at it. In which case, you're screwed. You could just be sitting around listening to records and then realize that he's kissing you. If you think of him as a potential lover, he's attainable. If you don't think of him as a potential lover, you'll be surprised one day. One of the best remedies to the mystery is the night out with friends. If he is visibly awkward about meeting people who may judge him harshly, he likes you. Scare him into figuring it out? Admittedly, that's the hardest one.
-Don't be a crazy cat lady. You know all the reasons why. Aside from companionship, that cat hair will never get out of your finest gowns.
-Last but not least, I put a call in, his mom will definitely pick you up, but he doesn't know about the date yet. Better get on it :)

Ladylipstick said...

Anonymous 1:52.- I hear that people in NYC meet offline, but Bostonians are too cold and antisocial for that!

Devon Ellington said...

Hey, I'm getting ready to move to the South-of-Boston area -- does that mean my dating life will be destroyed? ;)

Seriously, having spent most of my professional life in the theatre, you're much better off meeting men outside of it.

I usually find them when I'm not looking for them, often when I'm traveling or doing freelance work or covering a sports event or volunteering or wandering around an art museum because I need to fill up the creative well, and not thinking about dating.

Don't stick to any rules. Go with your gut. You'll know when to have sex; you'll know when to tell him things you're not going to tell in Minute One. As each person is an individual, so is each dating situation. When you get into rules and boxes, that's when it all goes to heck without the hand basket.

Get involved in things that are fun, and your natural enthusiasm winds up drawing interested guys to you.

There really are a lot of fascinating people out there, and you're not going to want to date/sleep with all of them, but if you give them a chance as human beings FIRST and let it evolve into dating or just hanging out without trying to force anything . . .it'll happen without the stress and worry.

Ladylipstick said...

Devon- don't worry, this post is 95% tongue-in-cheek.

leefilm said...

Any advise I offer is obviously prejudiced. Best of luck. Like your blog.