Two Guys = One Good Relationship?

We chat at 1 p.m. today.

Hi Meredith,

I'm an active reader of Love Letters. I've never reached out to anyone about any of my woes, as I keep most of my personal life private. However, over the last few months I think I have gotten myself into a bit of a situation and need to know if it's going to emotionally crush me.

My last relationship ended very badly about 16 months ago, and while I've healed from those wounds I would say that I'm not the same person. I've taken the last year to focus on myself, and in January I started causally dating again. Since then, I've met two wonderful guys. One of them is "Tony." We went on a couple of dates before I got the dreaded "just friends" text. He explained to me that he wasn't in a great place for a relationship and really needed some friends in his life. Despite it stinging (because I had and have feelings for him), I believe he was being genuine with me. Regardless, we talk every day and see each other once a week and I am happy with that.

The second guy, "Arthur," and I have quite a different relationship. He takes me on dates, we've been physically intimate a number of times, we've slept at each other's places, and are generally affectionate when together. I have taken a cautious approach with him, and we've both agreed that there aren't any expectations for where it's going. Arthur has a demanding job, so we mostly see each other on weekends and exchange texts once a day. I know he enjoys spending time with me, and I genuinely like him. I didn't develop feelings for him as quickly as I did for Tony, but there's still a connection between us.

At the end of the day, am I setting myself up for crazy heartbreak here? I have no commitment from either of them, and I know that I will want something more. Is this just dating? I'm in my 20s and so are both of these guys. Is this great for my age and life right now because I have a mostly-satisfying emotional relationship with Tony, and everything else with Arthur? The more I re-read this and think about it, the worse this situation seems. Help, please.

– Two-for-One Deal


Let's start with Arthur. You've been seeing him for a while now, and you've admitted to yourself that you want more. It's time to tell him that the "no expectations" thing isn't working for you. After getting to know him, you like him enough to consider a bigger relationship.

Something tells me, based on the weekend dates and the affection, that he'll be open to the conversation. Just make sure you're specific about what it would mean to get closer – whether there'd be more texts, an attempt to have mid-week dates, or maybe a promise of exclusivity.

As for Tony, you have to let go – or at least stop the daily conversations. You admit that you still have feelings for him and that you might be using the relationship to make up for what the other one lacks. Fake boyfriends are no good. You were never in it for a friendship.

This letter makes it clear that you're being honest with yourself. Now it's time to get real with everyone else. If this were a great situation for your age and lifestyle, you wouldn't be writing in to Love Letters.

Readers? Arthur? Tony?

– Meredith