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Articles by Drew Halsted

man upset girlfriend said penis is too small
WTF Should I Do?

My Girlfriend Said My Penis Is Too Small

September 7, 2026
The Couples Counseling Chicago editorial team researches and reviews products that may strengthen your relationship. We may earn a commission if you purchase through links in this article at no additional cost to you. The […]
woman snooping through boyfriends phone
WTF Should I Do?

I Snooped Through My Partner’s Phone and Found Something – WTF Should I Do?

September 1, 2026
The Confession Someone recently described the moment they realized they had crossed a line — and also found exactly what they were afraid of finding: “I snooped through my partner’s phone. I know I shouldn’t […]
person who is other person in a relationship looking at phone
WTF Should I Do?

I’m The Other Person in Someone’s Relationship — WTF Should I Do?

August 15, 2026
The Confession A counseling request recently came in from someone who was carrying a secret they did not know how to talk about: “I’m the other person in someone’s relationship. I didn’t mean for it […]
two people sitting on a park bench sharing a quiet moment that suggests possible romantic attraction
Relationship Resources for Couples

I’m in a Relationship But Attracted to Someone Else: What Does It Mean?

August 8, 2026
You’re in a relationship. Maybe you love your partner. Maybe nothing is technically wrong. And yet, someone else has your attention — a coworker, a friend, someone from your past, someone you follow online, someone […]
person looking in a mirror while feeling anxious about telling their spouse about secret credit card debt
WTF Should I Do?

I Charged $10,000 on My Husband’s Credit Card and He Doesn’t Know — WTF Should I Do?

July 25, 2026
The Confession A woman recently shared something that had been keeping her up at night: “I charged about $10,000 on my husband’s American Express card, mostly from shopping, and he doesn’t know yet. Money is […]
Two men sitting apart on a couch, reflecting emotional distance in their relationship.
WTF Should I Do?

Why Gay Male Relationships Struggle: 10 Patterns That Create Distance

July 20, 2026
Three weeks into dating someone, you already know his coffee order, his ex’s name, and roughly how many kids you’re supposed to have by 2032. It’s electric. It’s also, if you’re honest, a little fast. […]
man cheating questions
Relationship Resources for Couples

Is Fantasizing About Someone Else Cheating?

July 20, 2026
Does thinking about someone else count as being unfaithful? You are in a committed relationship, but every now and then your mind wanders to someone else. Maybe it is a coworker, an ex, a celebrity, […]
cute gay couple in love
Counseling Corner

5 Tips for Gay Men Considering an Open Relationship

July 20, 2026
Gay and considering an open relationship in Chicago? By: Couples Counseling Staff LGBT Pride month in Chicago is behind us, but the thoughts of the men that you saw at the parade or fest may […]
man sleeping with his boss and likes it.
WTF Should I Do?

I’m Sleeping With My Boss But Feel Weird

July 5, 2026
I’m Sleeping With My Boss and It Feels Amazing — So Why Do I Feel Weird? A reader recently wrote in with a situation that sounded exciting on the surface but emotionally complicated underneath: I’m […]
man under distress after getting caught having an affair
WTF Should I Do?

I Got Caught Having an Affair – WTF Should I Do?

June 30, 2026
If you are reading this, there is a good chance the affair just came out. Maybe your partner found a text. Maybe they saw your face when their phone buzzed. Maybe you finally told the […]
couple reviewing bills after paying adult child rent
WTF Should I Do?

I’ve Been Paying My Adult Son’s Rent and Now I Have No Retirement — WTF Should I Do?

June 29, 2026
You started out helping. Maybe it was only supposed to be a few months. A job loss. A breakup. A mental health rough patch. A bad lease that fell apart at the worst possible time. […]
Boundaries vs. Controlling Behaviors
Relationship Resources for Couples

Boundaries vs. Controlling Behavior: How Couples Can Tell the Difference

June 29, 2026
Boundaries vs. Controlling Behaviors “I’m just setting a boundary.” It’s one of the most common phrases we hear in couples counseling — and one of the most misused. Sometimes it’s exactly right: a partner naming […]

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