Chicago Sun-Times

There may be more to pal’s sloppy appearance

Tue, 01 Oct 2013 10:32:28 -0500

Is there a tactful way to suggest to a friend that a makeover would do wonders for her?

A friend is dating a friend, but one’s keeping a secret

Sun, 29 Sep 2013 18:46:00 -0500

Dear Cheryl, I have a dilemma. At a party at my house, one of my good friends, Shelly, hooked up with one of my husband’s good friends, Ted. (I’ve been friends with Shelly for 10 years. My husband has been friends with Ted for 25 years.) The two of them have been in a relationship for about a year now. Recently, while trolling Facebook, Shelly noticed a post in which Ted’s ex-wife commented that her daughter (Ted’s ex-stepdaughter) hates Ted for good reason. Shelly questioned Ted, who stated that his ex-wife is crazy and left it at that. I told …

Blended family life is never easy

Wed, 25 Sep 2013 13:06:01 -0500

Marriage is tough. Raising children is tough. Raising someone else’s children is often a deal-breaker in second and third marriages. Today some stepparents offer advice on making it work:

She did everything right, but things went wrong

Tue, 24 Sep 2013 08:38:00 -0500

Did you ever do everything right and it still came out wrong?

A teacher only dates on weekends when he doesn’t have his kids

Wed, 18 Sep 2013 17:26:00 -0500

Many of you had concerns about Greg, the 43-year-old teacher with custody of his kids. He only dates every other weekend when his kids are with their mother. He’s getting serious about Joy and you had reservations.

Dating, marriage can be challenges for single parents

Tue, 17 Sep 2013 10:46:34 -0500

Some things just don’t mix. Chocolate and sardines. Caramels and dentures. Children and dating. Should you introduce your kids to your date? If so, when? What if you remarry? What role will your new spouse play in your kids’ lives? Parent? Friend? Boarder? Here are your thoughts . . . DENISE: When my daughter was 16 I was dating a man exclusively. I’d been divorced for awhile at this point. She’d met a few of my dates, but I never involved her in my romantic life. I thought that was best. But he was different. I thought we might actually …

Adjusting to the realities of male, female and other

Sun, 15 Sep 2013 16:08:00 -0500

The recent column about Jackie who was born a male but always felt she was a female has started a discussion about transgenders. Your thoughts ... MACI: My tween daughter signed up for a computer course which asked for her gender. The choices were Male, Female, and Other, with a space to specify the Other. I thought that was very telling of progress in this area, and it was an excellent opportunity to have the transgender conversation with both my kids. For many in the current young-adult generation and the generations coming up, this will become more and more of …

Ivy Leaguers not always the smartest

Wed, 11 Sep 2013 16:36:00 -0500

Does an Ivy League education mean you’re smart? Not necessarily.

Interact with lover on regular basis before committing

Tue, 10 Sep 2013 10:10:05 -0500

Greg was the divorced teacher with custody of his kids. He dated only every other weekend when his ex-wife had the children. He’s currently dating a woman and thinking of marrying her.

20 years out of the closet

Mon, 09 Sep 2013 08:04:40 -0500

September 26 will mark the 20th anniversary of Britney’s coming out as gay. Before that, she wasn’t really in the closet — she didn’t lead a double life — but she did fight her orientation.

Three strikes but not out

Thu, 05 Sep 2013 16:33:18 -0500

Greg is the 43-year-old divorced man with custody of his kids. He’s the teacher with the 9-year-old minivan with suspicious stains on the carpet. He’s the one who can’t get a date once women find out The Big Three: kids, teacher, minivan.

As times change, transgenders more comfortable living out in the open

Tue, 03 Sep 2013 08:43:42 -0500

As society becomes more liberal, there’s one group that’s starting to poke a foot out the closet: transgenders. A real-life transgender actress plays a transgender inmate Netflix’s “Orange is the New Black.” “Glee” had a transgender character. There were transgender characters on “Dirty Sexy Money,” “Nip/Tuck” and “Necessary Roughness.” Cher’s son Chaz was once her daughter Chastity. And convicted felon Bradley Edward Manning wants to be known as Chelsea Elizabeth Manning. Jackie isn’t an actress, the daughter of a celebrity or a criminal, but she is transgender. “I’m no longer in the closet, but I was for quite a while. …

Strike three and this guy is out

Sun, 01 Sep 2013 19:56:00 -0500

Greg is a 43-year-old divorced man. He’s 6-foot-5 and takes good care of himself. He says, “I’ve been complimented many times on my looks and healthy lifestyle.” And he can’t get a date.

Smarts are OK, smart attitude is not

Thu, 05 Sep 2013 16:33:18 -0500

We recently heard from I Can’t Help it if I’m too Succesful, a Harvard-educated single woman, 36, who said she “intimidated” most men because she was more successful than them. Here’s what readers had to say.

About to divorce, mom isn’t sure when to start dating

Thu, 05 Sep 2013 16:33:18 -0500

Dear Cheryl, I’m getting divorced soon. I’ve got a 3-year-old and a 5-year-old. I intend to start dating as soon as my soon-to-be-ex moves out of the house. I’m a working mom and don’t have a lot of free time. I like to spend as much time as I can with my kids. My question is how do I find time to date and be with my kids? Can I bring my kids along on casual dates to the movies or the beach? WANT TO DO IT RIGHT Dear WTDIR, The short answer is NO. The long answer is NO …

Taking time to make sure potential stepdad’s a good guy

Thu, 05 Sep 2013 16:33:18 -0500

CHERYL LAVIN: Today’s column is about stepfathers, potential stepfathers and a famous flasher.

When ending a relationship, a serial dater looks for the complete opposite in a match

Thu, 05 Sep 2013 16:33:18 -0500

Opposites attract when it comes to potential mates for a reader.

She thinks success is thwarting search for love

Thu, 05 Sep 2013 16:33:17 -0500

Dear Cheryl: I’m a single woman, never married, 36. I’d love to meet my soul mate and marry. I haven’t felt this way all my life. In my 20s and early 30s, I was busy completing my education and starting my career. Now that my education is finished and my career is well on its way, I’m ready to settle down. The problem is I intimidate men. I’m better educated, far more successful and make much more money than most men my age and even older. When I tell them where I went to school and what I do, they …