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.
BUY OUR BOOKS!