This interview is continued from “Interview with a Cougar, Part 2.“
…we somehow wound up in my bedroom. We were both heavily intoxicated and we wound up having sex. It was honestly the best sex I have had since….I honestly cannot remember when. After a few months of seeing each other (including a 3 some with his 20 year old friend) it kind of fizzled out. It was at this point I had apparently made a name for myself and had several young men in their late teens/early 20’s that were wanting to date me.
ODM: I see….so what exactly was it about 18 and 19 year old guys that did it for you?
Debra: At first it was the excitement of it all….then after a while it was really more about convenience than anything else. Everything was light and breezy….no pressure, no having to stress about going out or dealing with “issues” that most single men my age have. I did not need a man to take care of me financially, so that really only left one particular area that needed to be serviced.
ODM: What did your friends think?
Debra: I hang out with a loosely knit group of 30-40 year old professional women. We used to think of ourselves as the “LA version” of Sex and the City. Having a 19 year old boytoy by my side was just like rocking the latest Prada handbag. It was the one fashion accessory that most women my age could not get because Father Time had not been as kind to them as he was to me. A few of my friends who had sons that were 18 and 19 years old did frown upon it a bit but I paid them no attention. “Jealousy” was the first word that crossed my mind whenever someone said something negative…
ODM: So after the initial excitement died down….when did you start taking interest in seriously dating younger men for a committed relationship?
Debra: I would say probably after the first year or so. I only dated 4 guys in that period of time, and all were brief flings. I was at one of the local bars down in Newport Beach with a group of girlfriends. There was this one young man, impeccably dressed….and he had this air of confidence to himself that is normally found in professional men in their 50’s and 60’s. He was the one who approached me and we spent the entire night together drinking and dancing. He asked for my phone number at the end of the night and I really didn’t give it any second thought. I was not expecting him to call me back. Sure enough a few days later my phone rings and he was asking me out to dinner. One thing led to another and in a few short weeks we were boyfriend girlfriend. During the entire course of that relationship, it became very clear to me that dating younger men was the only way to go. An older man could NOT possibly give me everything this 25 year old had to offer. Great body, hot looks, funny, charming, not jaded, no ex-wife/alimony/child support baggage…..Just a great human being that loved to go out and enjoy life. Isn’t that what we are all looking for?
ODM: Are you still dating him?
Debra: No, it ended after about 8 months for reasons that I would rather not get into. We are still very good friends and I care a lot about him.
ODM: Are you single now?
ODM: Where do you go to find younger men? How do you go about approaching them without it turning into a potentially awkward moment?
Debra: Well, truth be told….there have been no awkward moments when it comes to picking up younger guys. If I’m out at a trendy bar or even at the supermarket I can tell right off the bat that they are into me. If I can compare men to books for a minute…..the “older” men in their 40’s and 50’s are kind of like an advanced Trigonometry math book. Hard as hell to understand their motives/intentions and even harder to force myself to like. Younger men in their late teens/early 20’s are kind of like a Dr. Seuss book. Fun, entertaining and by just looking at the cover of the book, you already know what it’s about. Hop on Pop; Green Eggs and Ham, Thank you Ma’am.
When a 20 year old guy is staring at you from across the way, it is a pretty forgone conclusion that he wants to talk to you. Most guys that age are typically shy and as such I find myself being the one having to initiate conversation and breaking the ice. These same guys have told me that it was so easy to talk to me and that they felt very comfortable from the minute I walked over there and started to chit-chat. They also have told me that it is not the same way when it comes to talking to women their own age.
ODM: Let’s talk about the “S” word for a minute….
Debra: (nervous laugh)
ODM: “Sugar Mommy”. Do you find that most younger guys expect you to pay their way and shower them with gifts and whatnot?
Debra: Honestly? No. Most guys that age are poor, broke college students and are somewhat shy about going out because they feel that they have to pay because they are the guy. I make it a point to let them know from the start that I realize that they are just starting out in life and I have no problem footing the bill most (read: all) of the time. They seem to like it. My last boyfriend was a sophomore in college and was working as a waiter making minimum wage and tips. I think that amounted to a little under $250 a week in take-home. I took him out one weekend to South Coast Plaza (an affluent mall located in Orange County, Ca. – Karen) and bought him $2500.00 worth of new clothes. About half of that was spent on dress clothes. I would also give him $500 a week in cash to spend on food/etc. Life is tough when you are in your early 20’s, going to school and working a crap job. I had the means to support him and I also cared very deeply for him….so why not?
ODM: Where there ever any indications that he was just using you for sex and money?
Debra: Never did that thought occur to me. You can pretty much tell within the first few dates if it is going to turn into a real relationship or just some fling. I’m over the “flings” and am looking for a real relationship.
ODM: Have you ever tried an online dating service?
Debra: I am currently a member of 2 online dating services. There seems to be one in particular that for whatever reason attracts younger men looking to date older women. With online dating, it is very easy to weed out the good ones from the bad ones and at the end of the night I’m not stuck with a $150 bar tab and a hangover the next morning.
ODM: So where do you see yourself in 5-10 years from now?
Debra: In a loving, committed relationship with a man 15-20 years my junior. I realize that society in general is becoming more liberal and accepting than it was 20 years ago. Although, there are still people out there who frown upon my choice of lifestyle. I realize this and as such try to keep my dating preferences a secret as much as I can. At the end of the day and when it is all said and done, all that matters is that you are spending the night with the person that makes you happy the most.
ODM: Do you have any thoughts for young men/older women who are looking to try dating each other?
Younger men: If it is just a sexual fantasy to “hook up” with an older woman, and you have no further intentions in life than that, please let them know from the beginning. Even though we are a bit “older”, we still have feelings. If you are looking for a relationship, be honest and treat us with respect. We have a lot to offer you (more than most women your age) and you will soon come to find out just how rewarding it is to be dating a woman that is older than you.
Cougars: This is it ladies. We have finally come to a point in life where we don’t need a man our age to take care of us financially. We are tired of the b.s. that is sometimes associated with dating men our own age. Be proud of the fact that you are a liberated, strong female and empower yourself in your daily life. When you are dating younger men, realize that even though they are younger, they are still men. There are good apples and there are bad apples. Keep your eyes open, and feet on the ground and when you do finally find that special guy you will find yourself experiencing a richness in life in ways you never thought imaginable.