Does a Relationship Have to Start Out Easy to Be Successful?

Hi Evan,
First off- thank-you! I am a single mom and finally find myself in a relationship with another single parent whom I completely respect and trust. Your advice on waiting to have sex until committed, mirroring, and letting him lead the way have 100% worked for me!

Here’s the rub. We have been together 4 months. 1 month in he lost his job, 2 months in his car, and at 3 months was just barely managing to hang on to his home.

He is also building his own business from the ground up and is finally seeing an income again. His stress level is high and his schedule is intense. He is spending all of his free time with me, however, that’s only 1-2 nights a week. We do talk on the phone everyday.

I know he wants to be with me. I know he is overloaded. None of my needs are being met right now (companionship, regular sex). How do I hang on? Do I just grin and bear it? We have weathered quite a bit together in a short period of time and this isn’t exactly the smooth start to a relationship that I always hear is key to long-term success. Plus I feel our communication levels are getting lower, not higher due to everything piling on top of him. How do I gauge a relationship without all the ‘normal’ barometers?

Thanks for listening. —Alyssa

Dear Alyssa,

Ready for Lasting Love?
Ready for Lasting Love?

Thoughtful question, which resists an easy answer.

I think it all depends on whether you see this man as having the potential to be your future husband or not.

As long as you’re on his team, you have a great chance to weather this storm and prove your worth as a partner.

If you do, you stick it out.

If you don’t, it’s well within your right to bail.

First, take a look at the man himself. Most of us have gone through hard times in our lives, not unlike your boyfriend.

Some people pull out of them — some people are in a perpetual funk.

Which category does your boyfriend fall into?

Is he a strong, driven, entrepreneurial man with a combination of book smarts, street smarts and drive that will lift him from his malaise?

Or is he the kind of guy who is always bouncing from job to job, who always complains that no one understands him, and who always has big ideas that never quite take off?

In other words, do you believe that this man will eventually pull himself out of this rut and that you’ll get back to normal?

If you believe in him, then I would stick with him.


Not because he’s a load of laughs with a high sex drive and a lot of free time and disposable income, but because you believe in his character and are the kind of partner who values loyalty.

Flip it over for a second and imagine you were in his position. What would you like HIM to do? I assume that if you were in his position, you’d be busy, stressed, frustrated, worried, depressed and consumed with pulling yourself out of this financial hole. Everything else would, by nature, be secondary to you getting back on your feet.

You’d presumably want him to be patient with you as you work through this tough time. Or, you’d have the kindness and wherewithal to realize that you have nothing to give, that it’s going to be a LONG road back, and let him know that he should probably move on without you.

If you believe in him, then I would stick with him.

But if, as you acknowledge, he’s a good man who is already spending all of his free time with you, I would ask him how you can help him achieve his goals. Can you help with his business? His marketing? His accounting? The dinner/movie bills? When I met my wife, she was in deep credit card debt and I helped her out by taking care of every check for three years, until she paid down all of her cards.

As long as you’re on his team — not pressuring him or telling him how much he’s failing you — you have a great chance to weather this storm and prove your worth as a partner. And I can all but guarantee you, he’s never had someone who has done anything like that for him before.

This is why you’d choose a man. This is why he’ll choose you.

Good luck.