My poor mother. I think my singledom affects her more than anyone else. When she looks at me, I can see the sadness in her face: “where did I go wrong?” Back in the day, my mom had many suitors. She was married at 21 (engagement picture below), and by the time she was my age, she had 3 kids. And here I am, her daughter, in my late twenties, single, and without any prospects—the exact opposite of her.

I really don’t know how I want my mother to be involved in my dating life. For starters, she tells everyone about her finder’s fee of $1,000. (The match has to result in marriage, mind you.) But my mom is bi-polar when it comes to my dating. Whenever people suggests they know someone to set me up with it, my mom immediately says, “We’ll take him!” Another example: one time I was quietly inquiring about a guy at a family function. My mom was standing by listening, and when she heard he was a skier and going to med school, my mom shouts out loud, “Jenny, he’s the One!” It was like one of those moments when the jukebox stops, the whole room goes silent, and everyone turns their heads towards YOU.

But on the other hand, I’ve never dated anyone she’s really liked. “He’s a nice guy Jenny, but I just don’t think he’s it. She has even gone to the extreme of arranging a date when I was steadily seeing someone else. Tell me, how awkward is it when you are hanging out with your guy when some waiter she met last night calls to ask you out? Usually my boyfriends sensed what was going on and broke up with me first. (But thanks, Mom, it was a blessing in the end.)

My mom has a thing for waiters. She leaves my number on restaurant receipts. She tries to secretly give the waiter a nod in my direction. One time, she relentlessly pursued some cheesy beefcake from “SoCal” until he finally agreed to go out with me. (We have quite different tastes.)

Last week when we were eating at CPK, a quasi-cute, super-smiley waiter served our table. After he took our order with way too much enthusiasm, I looked at my mom and said, “NO!” before she could even say anything. She started laughing. “I know what you’re thinking, and NO!” If it were up to my mom, she would have asked the guy out there for me right on the spot.

Back in college, whenever I mention that I’ve met a new guy, she interjects, “well, did you tell him you’re a ski instructor at Deer Valley,” thinking the guy would immediately fall in love because I was a skier. “No Mom, my first words to the guy were not, ‘did you know I’m a ski instructor at Deer Valley?’” Sheesh.

Sometimes I tease my mom by saying, “Mom! I’ve met somebody!” and when she gets all excited, I then say “just kidding!” She tells me I’m too old to be joking about this anymore. She often threatens she’s going to take over the situation and put me in an arranged marriage.

But I try to take her behavior with a good heart. A lot of my motivation for finding a nice guy is not only to make me happy but also make my mom happy. She’s been through a lot in life, and I know she’ll rest easy if I marry a nice guy. I do believe moms have a sixth sense when it comes to their offspring. She’s been right about everyone so far. So when it comes down to the nitty gritty of dating, my mom is the only person I will really trust.

**So if you date Jenny, you’ll probably have to meet her mom, but probably not until you are practically engaged. That’s how both my older brothers handled it.