2 Tests to Determine if He’s Worthy Of Being Your Boyfriend

Paulina is in her early 50’s — thin, blond, whip-smart, and sophisticated. She worked with me last year and came back once she found a promising relationship.

She lives in Boston. Matthew lives in Atlanta. They met online and emailed regularly. Emails turned into phone conversations. Phone conversations turned into flirtation.

A few months later, they got together for a romantic weekend.

And ever since — surprise, surprise – he’s been a little bit emotionally distant.

Oh, he still calls and texts every day — little things like “how was your day?” or “I’m really tired” — but the spark is long gone.

Matthew no longer compliments Paulina. He no longer flirts with her. He mostly talks to her on the phone and complains about his life.

Most importantly, Matthew hasn’t made any overtures to see Paulina since their first meeting.

Distraught, Paulina is desperately trying to figure out how to rekindle their relationship.

Ready for Lasting Love?
Ready for Lasting Love?

Wait. Hold your thoughts.

When we talked about things, I learned that Matthew is a kind, attentive man, but he’s a bit socially awkward. He says things without thinking. Mostly clueless, selfish things, somewhat like a 12-year-old boy.

As a result, Paulina spends most of her relationship wondering why things can’t be better, easier, more fun, more supportive. Why can’t they be the way they were in the first couple of months, she asks?

My answer: Who F-ing Cares?!

As Paulina tells me her story, I get mad myself. Mad because of the way she’s being treated. Mad because she is perfectly willing to ignore the red flags. Mad because she’s not mad at all. She’s just sad. Lonely. Confused.

In short order, I asked Paulina to do three things:

Tell me what she likes about Matthew.

All I heard was negative stuff so far. I wanted to know what I was missing. Paulina thought for a second and said, “He’s simple. He can be sweet. And he does call or text me multiple times a day.”

Tell me what she loses if she cuts Matthew out of her life immediately.

After a bit of deliberation, she concluded that she loses two things:

a. His daily calls and texts, mostly boring chatter about his life.

Don’t mistake phone calls for dates. A man who wants to be your boyfriend MAKES PLANS to see you IMMEDIATELY.

b. The fantasy that this once-promising relationship would work out.

Not surprisingly, Paulina was having far more trouble losing her fantasy of a serious relationship than the texts.


The third thing I asked Paulina to do when we got off the phone?

Dump him. Because Matthew was failing not one, but BOTH long-term boyfriend tests.

Test 1: Is this fun? Is this easy? Do I enjoy the relationship? Am I happy?

Big fat NO. It doesn’t matter if there was attraction and flirtation three months ago; right now, Paulina is Matthew’s emotional booty call. He keeps in touch with her regularly to have a female presence in his life, but conversations aren’t fun, lively, playful, or even interesting. What is SHE getting out of this relationship? Nothing.

Test 2: Is he making an effort?

Big fat NO. Don’t mistake phone calls for dates. Paulina is Matthew’s pen pal. A man who wants to be your boyfriend makes plans to see you IMMEDIATELY. “What are you doing tomorrow? The next day? The following weekend? For Thanksgiving?”

That’s what we do when we want a serious relationship. Anything less, you’re settling for crumbs.

So if you look at your current relationship and find yourself in inner turmoil, chances are there are one of two things wrong:

1) You really don’t like the guy that much. You like the idea of the guy, but you don’t actually have a fun, supportive, easygoing partner in a committed relationship.

2) He’s making no effort to see you, commit to you, or grow your relationship.

Either one is grounds for dumping. If this applies to you, get started now.