20-Something Question: Honesty vs. Hurting Someone’s Feelings


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Q. 2013 proved to be a strange year of dating for me and as I look back on the occasionally meaningful, sometimes awkward and often forced exchanges I had with different men, I can’t help but feel frustrated and unsettled. At the end of the day, if I am being really and truly honest, it would be pretty darn great to meet a man, feel uncannily connected, fall in love, and seek new adventures with a partner by my side. The reality of the quest, however, is far more complicated.

Recently, I met a 20-something guy who was laid back, kind, hardworking, a good listener, fun to be around and easy to talk to. We instantly hit it off. Three days after we met he said, “I like you!” unabashed and with a proud, goofy grin. I could not help but reciprocate, in spite of myself. I was flattered and absolutely charmed by his forthrightness but I still wasn’t sure about how I felt. I liked him too! It was such a breath of fresh air to feel so comfortable with someone and enjoy answering questions and feeling curious about his answers. When he leaned in to kiss me at what would have been, honestly, the perfect moment in any classic rom-com to make a move, I leaned back and told him that I was sorry but I wasn’t interested in getting physical just yet. He was instantly confused and said as much. “How is it that we get along so well and you’ve shown me that you are interested but you’re keeping me at an arm’s length?” I knew that what I had said had merit but I felt tongue-tied and struggled explain in words what I felt so concretely in my gut.

I have grown more reserved and I didn’t want to dive in too quickly before knowing a little more about him and figuring out the true nature of my own feelingsI feel like I’ve fallen into a cycle of getting to know guys while also sleeping with them and it’s created false expectations and disappointment on all fronts. So I was completely honest and told him I was looking to try something different. “Can’t we just take some more time to get to know each other, first?” I asked. He respected my request but I could tell it had bruised his ego.

Over the next few days we made point of getting together. We continued to have a great time and he admitted he felt very strongly for me while my own feelings remained unclear. We had chemistry but I didn’t want to explore it just yet. I felt like we were running at two different speeds and while I think his feelings were very genuine, I began to feel like a tease and not being physical had somehow become this odd obstruction that garnered more attention that I thought it deserved. I don’t think holding off on being physical makes me a prude, a tease, a cynic, or “a girl with too many walls”. I’d like to think I’m just trying to be honest and not use intimacy as a crutch which is something I know that I, personally, have used many times in the past.

I suppose my question is, in light of this experience and many others like it, …how can I date and be honest without hurting others and also being true to myself? Finding  someone to love and love you back is messy. It’s hard to find a person  you’re on the same page with, which is, I suppose, what we’re eventually all looking for. But while I remain a hopeful player in this pursuit, I struggle to find a way to go about it honestly, kindly, and with grace.

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A. Dear 20-Something,

It sounds like you are confused. You say “I still wasn’t sure about how I felt. I liked him too!” at first and then you say you had chemistry buty you weren’t sure you were attractied to him. I applaud you deciding to take a different approach. You have to do what feels right to you and if you would like to wait longer to get intimate that is nothing to be apologetic about. It this case I just wonder if you just like the “unabashed” and unique experience of a guy being so interested and honest. It’s not common these days. It’s like wow…this doesn’t havppen very often…maybe I should like him. So how to be honest? Be honest with yourself first. Then second, don’t ask, tell. Just say I do like you but I am in a time in my life where I want to wait to get intimate. Period. It’s not a question of whether you like him or not …it is about what you are choosing to do in your life right now. I also wonder if a kiss goes against that? If you make it clear you are not gong to sleep with him a kiss could help you decide. I believe in the 3 date rule. Don’t dismiss someone after one date because when you get to know someone a little better they can get oh so much sexier. But after 3 if you don’t feel it don’t force it.


A. Dear 20-Something,

Maybe you are overthinking it. Liking someone doesn’t equal attraction. There is nothing wrong with holding off on intimacy. Being honest doesn’t have to hurt someone’s feelings. Just say how you feel and keep talking. Get to know him better. I never had any success trying to will myself to like someone. It just doesn’t work. Get to know him better and if you have some things in common then maybe he has a friend with the same values who you do find attractive. So you let him know you are interested in a friendship.


A. Dear 20-Something,

If it was such a perfect rom-com moment – you both had to have gotten there? If you didn’t want to kiss him in a perfect moment that says something. It’s easy to get caught up in the moment so I’m not being hard on you but if after time if you like him but don’t want to kiss him…that is not chemistry. And you can’t base a relationship one someone liking you.


A. Dear 20-Something,

Being honest is hard sometimes. But you don’t want to waste your time or anyone else’s on something you don’t believe in. I used to have a hard time breaking up with people because I didn’t want to hurt their feelings. It didn’t help either party in the long run. I actually fell in love with the person I was able to be completely honest with…and I did tell him we were on different speeds after our first date.. We stopped seeing eachother for a while but then I missed his presence. It wasn’t a dramatic…I want to get him back, I miss having someone liking me. I was that something was missing. May not work for everyone but the point that I was completely honest and direct was quite freeing and interesting that it led to a rich relationship in the long run. So take off the cushions and do be honest. When it is right it will be right.

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