KIRSTEN ULVE

Dear Dategirl,

I have been dating my ex-boyfriend since Christmas. He is 12 years older than I am, and I'm completely in love with him. Actually, I never got over him, so I'm ecstatic he's back in my life.

Here's the problem: He is a well-documented cheater. He cheated on his wife, on various girlfriends, and yes, on me....I know what you are thinking, and you are right.

Of course, people can change, but at the same time, if I let him hurt me again, I am going to feel like a total idiot. Am I wrong to not fully trust him? I want to believe that he will be able to stay faithful, but I know that if I can't completely trust him now, we are off to a bad start.

I realize that if we don't work out I have my whole life ahead of me. I'm only 22! But I really love him and want to give it a try.

Maybe I'm just overanalyzing this whole thing and am getting ahead of myself. What do you think? Should I give it a try again or leave now? I love him and want to be with him, but I don't want to get hurt again.Cautiously Optimistic

I'm not a proponent of the "once a cheater, always a cheater" mind-set; however, nor do I think you should leap blindly into a relationship with someone who has already betrayed your trust.

But let's put aside the cheating issue for a second to examine the age disparity, shall we? I also dated someone much older when I was about your age. My tendency—and don't make my mistake—was to think along the lines of 12 years older/12 years wiser. I wound up doubting myself and deferring to him far too often because of his advanced age and experience. I was wrong, and found out just how wrong at his memorial service when his "new" girlfriend explained to a packed house that there had been some serious overlap between us. My point is, people can be jerks at any age, so don't let him bully you.

If this man is committed to being with you, he has to realize that he needs to rebuild the trust he used to wipe his ass those many months ago. To do this, he has to maintain a certain amount of transparency. I'm not saying you should go nuts checking up on him all the time, but he should willingly hand over his cell phone when you ask for it. He should give up his passwords and not get bent out of shape if you take a gander through his e-mail on occasion. Not only that, he should understand when you need a little bit of extra assurance every now and again. I'm not suggesting you become a paranoid basket case, but the guy has a shitty track record and it's up to him—not you—to fix that.

I am a woman in my mid-50s going through a divorce. Now that I'm at a crossroads, I'm reconsidering my choices in work. I've thought about teaching, but wonder if I'll ever meet an eligible man my age in a school setting. I can't seem to get the idea out of my head that I might be better off choosing a career that will put me somewhere in the vicinity of interesting (unmarried) men if I ever want to get a date again.

Should I stay in my comfortable, familiar home and risk being a spinster kindergarten teacher, or should I listen to the little voice that's telling me to get out in the world and expand my horizons?Lucia

Let's consider the traditionally male-dominated fields—the prison system is one. Have you ever watched Oz? Plenty of men there. Construction, too. Ooh, and sanitation! Is potentially meeting a man at work worth wrangling prisoners, wielding a hammer, or scooping up doody? Answer: No!

Take the job that makes you happy (because happy ladies are pretty ladies) and meet men the way the rest of us do—online.

Judy McGuire is the author of How Not to Date. Dating dilemmas? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.