‘I’ve known her as long as I can remember’

Let's hang out at Wellesley Books tomorrow. Bring friends. There will be snacks.

Podcast Episode 4 is up ... and it's about a euro.

I have this friend; I've known her as long as I can remember. She lives in another city, but our families are close. She recommended that I go to her college. We now go to school together and hang out a lot. We talk, watch movies, etc.

I'm falling for her but not sure if I should go for it. It's hard to know how she feels. She manages an illness that has her severely depressed and severely hyper at times.

I think she likes to keep things from me, maybe because she doesn't want me to pursue a relationship with her. For instance, she has never mentioned anything about her previous relationships. I find out more from her friends, who told me she'd been dating an older man.

The more I think about it, the more I realize how important she is to me and how I love every quality about her. I can't imagine what my life would be like without her. That's why I'm so concerned about ruining a friendship. But at the same time, maybe pursuing this would end the awkwardness we have at times, and turn this into something good. I could really use some help about where to go from here.

- Falling


If these romantic feelings have taken over your brain, you should have a conversation with her about where you stand and how to proceed. Be honest with her, but consider these dos and don'ts:

1. Do not tell her you're madly in love with her (or make any other big proclamations) because it's too early to know what's happening here. Your feelings might seem big, but you have no idea what it would be like to date her. All you can say for sure is that you think about it, and that if she's open to it, you'd like to try.
2. Do let her know that if these feelings are not reciprocated – or she's not sure how she feels – you will continue to treat her well and respect her wishes.
3. Do make it clear that you will always put your history first. Your families are friends, and she's been a part of your life for a very long time. You will consider that history when making decisions about your future.
4. Do accept that if the feelings aren't reciprocated, you (or she) might need some space, and that's OK. It doesn't mean the friendship is over.

I can't tell you what she'll say, but at the very least, it'll be a lesson in communication for both of you. Now that you're in the same place and sharing so many experiences, it would be nice to be able to really talk.

– Meredith

Readers? Why doesn't the letter writer hear about her dating history?