I Want More Answers Before Really Dating Him

Chat at 1 p.m. Also, what’s going on with your love life right now? Send your own relationship/dating questions/problems to [email protected] or fill out this form, please.  And … are you a former letter writer? Tell us what happened after you wrote in (even if your letter was recent). You can ask Part 2 questions or tell us whether our advice was any good. Email [email protected] with “update” in the subject line. Also tell me what email address you used to send your original letter.


Hi Meredith,

I am struggling to decide whether to pursue a man in my life.

I previously told him that I needed to go slow so I can figure out if I really liked him. We started talking about this recently, and he told me that back then, he was super interested in pursuing a relationship, but as a result of me communicating that I needed time to see if I really liked him, he had pulled back for fear of being hurt.

He has always been super patient, open, and respectful of me and my time. He makes me happy and we can do anything together, whether it is cooking, hiking, or grocery shopping.

We currently function as a friends-with-benefits and can openly sleep with other people as long as we mention it to one another. I know I don’t want a relationship yet, as I’m still learning who he is as a person, but eventually do want something more. I guess I struggle because learning that he sleeps with other people does make me feel bad. I want something more exclusive and I’m not sure if he is willing to give me that now, nor do I know how to ask for it since he is protecting himself from getting hurt.

I’m not sure how to progress but I can definitely see myself with him. Any advice would be appreciated!

– XO


It took me a really long time to learn this, but there’s no way to get all your questions about someone answered before dating them. Even if you’re friends with someone for years before pursuing a relationship, you’ll still be vulnerable. You still might learn things you don’t like.

It’s frustrating and a little scary, but getting to know someone as a possible significant other often means trying it out. After gathering some basic information, sometimes you need to listen to your gut and jump in, making decisions as you go.

In your case, this is the time to say, “I see myself with you. I want to be with you – exclusively – because you make me happy. Can we try it and see how it feels?” He might hesitate, and maybe he’ll need time to think after all this time, but at least you’ll have stated your intentions.

Also be clear about what would be different, other than not sleeping with others. How would your mindset and behavior change? What are you asking for?

If he doesn’t want to try exclusivity and prefers the current arrangement, you might want to rethink the boundaries of your relationship. You don’t want to share him with others. It doesn’t feel good. Maybe you’re more interested in finding someone you can get to know while the relationship is in progress. Maybe not pursuing this in a real way has been you following your gut this whole time.

– Meredith

Readers? Any reason to wait with this request? Thoughts on the path to exclusivity for this LW?

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