Is an old bird in the hand worth more than a young one in the bush?

Biff Humble

Editor's Note:
Dear Readers,
Back from his long absence, Biff has dug into the huge pile of letters seeking his advice:

Dear Biff,

I am in my mid-20s, and in my first real "career" job. It's exciting and fast-paced, and I work with very interesting people. One of them is a 40-something woman, who, while not my supervisor, is substantially higher on the corporate ladder than I.

On a recent out-of-town business trip, she had a few drinks, and made a pass at me. I laughed it off and managed to difuse the situation without offending her. Since then, she keeps giving me "meaningful" glances when we are in meetings together, and once, when leaving a room behind me, patted me on the butt. It seems obvious that she's interested in me, which is not all bad, as, for a 40-something, she's pretty hot.

The problem is, there is another woman in my department who I kind of have a crush on. She's much more appropriate for me to date: same "level" as me, same age, and we even share some interests. She is rather shy, but approaches me to talk on occasion.

So, here's the quandary: I really like this younger woman, but she seems a bit "conservative." I can see myself dating her for quite a while before being able to "make a move." The older woman, on the other hand, I'm pretty sure would be "good to go" from the start.

What do I do, go for the sure thing (which probably has no long-term future), or take it slow with the one I might be able to have a meaningful relationship with?

Stalked by a cougar


Dear Cooter

Let me think about this for a minute:

Woman #1 is "conservative." I take that to mean you think you might spend hundreds of dollars wining and dining her, and still not get anywhere.

Woman #2 has proven herself as likely to spread her legs as a drunken prom date. And, "for a 40-something, she's pretty hot."

Seems like a no-brainer to me.

Especially when you take into account Biff's Rule of Romance #1:

"Young and pretty provides the thrills, but old and lonely pays the bills."

Normally, a man must make a decision when pursuing romance. What makes an older, wealthy woman attractive is that she will generously support a lifestyle a man cannot afford on his own. What makes a hot young thing attractive is that she's ... well ... attractive. But that beauty will often cost you much more than you get out of it (see my previous columns on the beauty:bullshit ratio).

In this case, Woman #2 sounds like the best of both worlds: She's hot; she'll likely pay for dinner; and she'll put out.

But, you can always follow the advice of an experienced gambler, and hedge your bet. It's quite likely this older woman will not want your affair to be public knowledge in the workplace. So, you could ask the younger woman out as well, and tell her you don't want the fact you are seeing each other socially to be public knowledge among your coworkers. Then, you can spend your time working through the defenses of the younger woman while releasing pressure with the older woman.

I don't think either of them would mind if they found out.

I hope this helps,

Biff

p.s. If you decide to go for woman #1, send me contact info for woman #2. Cash has been a bit tight lately.
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I'm smart and pretty, why don't men like me?

Biff Humble

Editor's Note:
Dear Readers,
Back from his long absence, Biff has dug into the huge pile of letters seeking his advice:

Dear Biff,

I'm a 30-something woman who's been quite successful in life. I have a master's degree and a great job; I travel; I'm in great health and in perfect shape. People tell me I'm fun, smart, and pretty. I'm happy with all the aspects of my life except I can't seem to find love.

I've tried to meet men in a variety of places: in class, at work, through friends, at events, and online, and sometimes I'll get a couple dates. Then the guy wants casual sex, making it obvious he has no interest in a relationship with me. I'm left confused and am becoming bitter, because I really want a relationship.

It would seem that being an attractive, accomplished person would make a person good relationship material, but apparently that's not enough. I have met a lot of women who are not as nice, less funny, and less interesting who manage to find boyfriends. What can I do differently that will make guys want to be in a relationship with me?

Perkie in Pokipsee


Dear Pokie

You are correct, being an attractive, accomplished person would make a person good relationship material, but that's just not enough.

You also have to NOT be a self-centered, egotistical bitch who thinks of others as "not as nice, less funny, and less interesting" than herself.

We at Red Flag Publishing have developed a theory to explain this to the clueless women who need to buy books such as "He's Just Not that Into You." We call it the Beauty:Bullshit ratio. It works this way: every man is willing to put up with a certain level of bullshit in order to obtain a steady source of sex.

There is a direct correlation between the beauty of the piece he is tapping and the level of bullshit a man is willing to put up with. A smokin' hot supermodel can be pretty much batshit crazy and still find someone with which to be in a relationship. But, even then, sometimes it gets too much and, although men all over the world shake their heads in disbelief, some guy actually breaks up with a supermodel.

You can't help but look at that situation, and wonder what kind of crazy is wrapped up in that slinky black dress.

So, our guess is that either you are not nearly as attractive as you believe, or it's obvious to men that there is a whole lotta crazy emanating from you.

We are guessing it's the latter, since the men you date are willing to have casual sex with you, but not subject themselves to a relationship with you. After all, it can be kinda fun tapping the crazy ones. As long as you don't do something stupid, like fall asleep before she does.

I hope this helps,

Biff

p.s. If you'd like to knock off a quick one, email me.


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