Love Letters: Can I Have ‘The Talk’ At Three Months?

Hi Meredith,

Long-time reader, first-time writer.

I'm a 33-year-old professional woman with a job I love and a great group of friends. I've been out of the dating scene for a while because, honestly, no one seemed worth my time. I had a fairly specific idea of what I wanted in a man: slightly older, successful business man (lawyer, finance, sales, etc), with a good degree, strong family values, drug free.

After my two-year relationship ended when I was 27 (yes ... it has been THAT long), I took some time for myself. Counseling (I have/had self-esteem issues), travel, friends -- typical "finding myself" adventures. I dated here and there, mostly from online sites, but never found anyone worth my time.

Until recently. Three months ago I went on a first date with "Phil." I fully admit that the first date was awful. I'm a fairly shy and quiet person, but he was even more quiet. I led the conversation and was the loud one. I was convinced that there was no chemistry. But to my surprise, as he walked me to my car, he kissed me. I decided to give him another chance. The second date proved to be a complete 180 from the initial meeting. He was talkative, funny, engaging, and sweet. We spent hours just sitting there at the bar talking. It was great.

So why am I writing? Because I'm confused. We've gone on many dates in the past three months. They've all been great and have included a few sleepovers, which were amazing. But I want more. I want to have "the talk." I want to commit to him and him to me. But after three months of dating and trying to keep it breezy and light, how do I bring it up without scaring him off? We've had conversations where we've admitted that we like each other a lot, but how do I approach telling him that there's no one else for me?

– Awful at Dating, North of Boston

If you're sleeping with him, you can ask whether he's sleeping with others. You can talk about exclusivity and and tell him that you're really enjoying your time together.

But you can't ask for proclamations of big feelings. Yes, you're super into him right now, but it's only been three months. Don't try to hit the fast-forward button. Who knows how you'll feel in another few weeks? All you know is that you really like him right now.

Think about what you really want at the moment (more dates, a promise that he’s not sleeping around), and ask specific questions. Nothing that requires making guesses about the future. And please try to enjoy the present. It sounds like you're having a great time.

Readers? How can she slow this down in her head? Does she need to? Does she have to pretend to be breezy forever? When should she have the talk?

– Meredith