Lunch is Not a Date

Lately, I’ve had people email me asking if someone is too young or too old for them. They ask whether they are too old to troll bars (if you have to ask, yes, you are too old) or too young to go to certain bars. They ask if they should be attracted to older or younger co-workers. It all really boils down to one question: What is your dating age range? How do you determine it?

First and foremost, realize that dating age range has little to do with your age once you are an adult. It is autonomous to each person. In short, your dating age range has nothing to do with anyone else’s, save the person who you are interested in or dating.

In my early twenties, I tended to find myself interested mostly in women who were in their early thirties. This was because I had already traveled extensively as a comedian, seen a lot, and had lots of experiences. Women my own age had little in common with me, whereas women in their early thirties had about the same life experience as me.

Now, just hitting my mid-thirties, I find myself interested in women in their early to mid-twenties. Why? No doubt every woman out there immediately thought, Yeah, because they are young and firm. Actually, some of the firmest, best-shaped women I’ve been with have been in their forties–nothing fake or fixed, they just stay in shape.

I lean toward younger women right now because I am in the midst of making some life-changes, like working on a new career (author, columnist, and web designer–if I ever finish learning Dreamweaver, Flash, and all the other junk), starting to get ready to save and buy a place, and that sort of thing. Lots of women I meet my own age already have a long-since-set career and a condo. They tend to be sick of their job, usually taken simply for the paycheck, and have little passion for it. They are also often downbeat about dating in general. One woman I dated recently responded with glares of skepticism whenever I complimented her during sex. It is annoying and a complete turn-off to tell someone she is beautiful and then watch her frown, followed by her reply–”You don’t have to say that, I’m already naked.” That gets old, tired, and annoying fast. It’s not only skeptical but insulting to my judgment. What, I can’t tell who I’m attracted to and need her to point out her flaws while we’re fooling around?

I am obviously very upbeat about dating and my career; I have a low tolerance for women who aren’t, when it comes to dating them. I relax, have fun, and don’t worry about any dating norms, stupid society rules, or maneuvering tactics; I also don’t greet my dates and anything they say or do with immediate skepticism. I also play a lot of sports in adult sports leagues and keep very socially active. Again, these traits tend to be shared with me more by women in their early twenties than by women my own age. (Many women my own age prefer to sit at home, catching up on TiVo instead of playing sports or being social.)

So, determine your dating age range not by your age but by where you are at in life. I am at a place in my life right now where dating significantly younger tends to be the current theme. That may very well change, as I am also interested in settling down, and younger women may not share that trait with me, yet. When it comes down to it, I’m not really dating or interested in an age; I’m interested in a person. (For example, just because I tend to date young right now, doesn’t mean I date women who like to hit the club scene or hop from one party or bar to another all night long, endlessly. Not for me and many I’ve met follow that pattern, so I am not attracted to them.)

Date where you’re at in life. You’ll be happier than trying to force yourself to date where you think you should be dating or worse, where your friends and family think you should be dating.

Last Autumn, my stepfather passed away. I originally posted this entry to my old site in memory of him. It’s good advice that I wanted to make sure was up here, too. 

I learned some key things about women and relationships from Rudy. They bear repeating.

“If you try to understand a woman, it’s your own damn fault.” Rudy told me that when I was in my early twenties, upset about a woman who had hurt me. (”Laura” in the book.) What he was really saying was that women are emotional. There will be many times when a woman acts out of emotion instead of rationale; don’t try to understand it. Accept it. Empathize with it. Ignore it. Be pissed about it. But never, ever, try to understand it; because, as a man, you won’t.

“A lot of people like me. A lot of people don’t. I try to spend as much time as possible with the ones who like me and as little with the ones who don’t.” When you think about it, it’s surprising how much time we spend trying to make people like us. Why? Spend that time with people who do like you. Dating isn’t any different. If you find yourself spending a lot of time trying to convince a guy to like you or chasing a woman who keeps turning you down, open your eyes; re-invest that time in someone who shows interest.

Here’s a catchy little line that gets a laugh and starts a conversation. I haven’t used lines in years but I did use this one a few times and Rudy swore by it. It’s very laid back, which is a big part of why it works. Approach a woman and ask, “If I won millions in the lottery, would you run away with me?” The woman almost always replies positively. “Can I borrow a dollar?” When she looks at you inquisitively, reply, “To buy the lottery ticket.” This gets a laugh and then leads to a conversation. On the off chance that she says “no” to running away with you, reply, “See, this is why you’re single. How much would I have to have for you to run away with me?” Banter with her. Chances are she’ll mumble something about there not being enough money in the world for her to run away with her. Tell her, “Good, because I don’t have enough to even pay for the drink I’m about to buy you.” As long as you get a laugh somewhere along the way, you can get a conversation going. If you don’t get a laugh, hey, read the entry before this one–”A lot of people like me. A lot of people don’t…”

Dirty jokes work on women. Rudy told tons. Women always fell for them, including my mom–who supposedly hated dirty jokes. It’s all about the timing and delivery. Here’s one that’s actually pretty clean: Three couples go to see a priest about joining the Catholic church. He tells them in order to join the church, they will have to give up something dear to them to show their loyalty to God. He decides that they must give up sex for thirty days. After thirty days, the reluctant couples return to see the priest. He asks them how it went. The first couple replies, “Man, it was tough; we had a really hard time, especially on the twentieth day. Wow, she was looking hot that day, but we hung in there and we didn’t have sex for thirty days.” “Welcome to the Catholic Church. And you?” “It was tough, really, really, really tough, but we did not have sex for thirty days.” The priest welcomes the second couple, as well. He then asks the third couple, “How about you?” The guy shakes his head, “Man, we were doing really well but then on the twenty-third day, she dropped an apple. When she bent over to pick it up, I just snapped. I took her right then and there. It was the most passionate, hottest, loudest lovemaking we’ve ever had.” “Okay, well, I’m sorry but you’re not going to be able to get into the church.” The guy scuffs, “Pfft, yeah, we’re having trouble getting back into the supermarket, too.”

What I learned most from Rudy was that when it comes right down to it with relationships with women, it’s not about money, looks, or style. It’s about showing them you are thinking of them. You do that by surprising them with a gift or date that relates to something they mentioned in passing, which they thought you never even noticed. Do something romantic every now and then. Rudy faired far better with women by surprising them with a picnic in a park or with roller skates to go on a surprise skating date, than other guys who dressed sharply, dropped a heavy dime, and spent their time talking about their own accomplishments. Pay attention to the woman.  It really is that easy.  (That doesn’t mean be a sap or “nice guy.”)

Here’s a little trick Rudy used that might work in your area. He found out where the airlines put up stewardesses. He became friends with the desk clerks of those hotels and they gave him a call whenever a few strikingly girls landed. Rudy then went to their room and offered to show them the town. Of course, that was years ago. Nowadays, you’ll have to put a spin on it in order to make it work; you probably won’t be able to get hotel room numbers flat out. Use your imagination; maybe you can find out where the flight attendants eat or what time their flights are landing–that would be key because you could be in the lobby when they arrive.

Most of all from Rudy, I learned that life is short and to enjoy it. I live everyday to its fullest and discovered after his death, from his good friends and neighbors, that he thought highly of me and my approach to life. He was happy for me, that I was able to travel as a comedian during my “early years” and that I have a book out, which is selling well and helping others lead happier lives. It makes sense, since, in a way, I’m really trying to teach people what he taught me. “Tomorrow is not another day; tomorrow is today’s backup plan.” That philosophy of mine came from a combination of myself, Rudy, and “Carpe diem” from Dead Poets Society. I thought highly of you, too, Rudy. Thanks for all the advice and for being there when I needed it. I will do my best to spread your philosophy and keep it alive.

Q: I met a guy waiting for the bus yesterday. He was very charming and interesting. We had a nice conversation while we waited for the bus. When the bus did arrive, I was totally turned off. He stepped in front of me to get on first. How rude! I was so annoyed I didn’t sit next to him. Why are men so impolite, and if I see him again, what should I do?
— CTA rider

A: That’s great that you met a guy waiting for the bus. It’s a good place to meet someone. No noise, no distractions, no other guys interrupting, none of your or his friends to worry about appeasing. And he must have some confidence to approach you, out in the open where he could easily and noticeably be embarrassed. Plus, if you’re unresponsive, he has to stand there next to you, waiting for the bus. He was willing to take that risk, so, there’s a good chance he’s a good find, at least enough of one to warrant talking more with him.

Good guys want to determine your level of interest. We’ll do minor things to see how you react, to make sure we’re not bothering you. If I meet a woman at a bus stop and we have a nice conversation and she’s laughing, but I sense she’s a little hesitant, I want to gauge her interest. A great way to do that is for me to get on the bus just ahead of her. Why? I want to see where she sits or stands. My plan is to grab a seat next to an empty seat or move toward the back of the bus. Does she sit next to me? Does she follow to the back of the bus or stay near the front? If she sits next to me or follows, I take it as a very good sign that she is at the very least interested in talking more. If she doesn’t, I take it as an indicator that she does not want to talk further and has no interest. I have to get on just in front of her, because if I don’t, some idiot who’s not paying attention might sit next to me or get between us. Maybe he wasn’t being rude, he was simply trying to gauge your interest.

If you see him again, realize he probably thinks you are not interested. You’ll have to approach him. Ask him how he’s been doing. He’ll take if from there. When you get on the bus, see what happens. If he gets on first, sit or stand next to him. If you get on first, get on just in front of him and sit next to an empty seat or push to the back and see if he follows. Give him something to work with!

Q: I just started dating this woman, and I’m a little nervous. She’s the first woman I’ve dated who’s older than me. I’m 23 and she’s 27. I don’t have much money, and she makes tons. How can I keep her interested, and what are some good date ideas?
— Too young?

A: Met her doing some charity at a nursing home, eh? Don’t sweat it. Simple dates like renting a movie or cooking dinner work just fine. Every now and then do something special. That doesn’t mean spend a lot of money, it means show her you listen to what she says. Women want that more than anything else. I once dated someone who grew up on a farm and mentioned in passing she had never been trick-or-treating. For one date, I went out and filled up my nephew’s plastic pumpkin with all kinds of candy, even the crappy kisses, candy corn and pennies we used to get as kids. We spent the date with me showing her how we separated and counted the candy as kids. She loved it.

Q: I’m a guy plagued by the fantasy all men have. I’d like to have a threesome. But really, really badly, like beyond most guys desires for one. Any ideas on how to make that happen?
— Wishful Thinking

A: A threesome doesn’t occur the way guys think it does. Most guys think the women don’t know each other, there’s some crazy pillow fight involved, and so forth. In reality, usually the women are really tight friends, and the guy is the stranger. Women talk a lot more about sex and relationships than guys, and in much greater detail, so it’s not unlikely for two good girlfriends to discuss it. Your best bet is to find two women who are really close friends at a bar or party one night who are behaving very flirtatiously. Flirt with them constantly, push a little more, add innuendo about the subject of threesomes to the conversation and see how they react it. If they don’t drown you in their drinks but instead react like the topic is no big thing, keep going, and at some point, make a pass at both, maybe by asking who is a better kisser. You’ll have to get the three of you alone at some point, so try to leave together and suggest sharing a cab or walking them home. Or just answer an ad.

This week’s column is about the danger of trying too hard to take care of someone you love. You may even say someone loved somebody else too much. Be careful. You can’t protect someone from everything and often you don’t even need to; don’t let this happen to you. The column is here:

 www.saveinheritance.com