When two people start off as friends, there is usually a good reason. Perhaps one of them is not attracted to the other, or they have a friend in common one of them has dated, or they were in a relationship when they met, or maybe they work together. Otherwise, they’d be dating, right? But there are times when someone you do not want to date can start off as a friend and impress you so much that you want to get closer.

Is it worth it? Does it usually work? Can a woman grow attracted to someone she was not initially attracted to? How does a man take the next step? I put these questions to a number of people who made it work. Let’s hear from women and men who made the jump from friendship to relationship.

A friend in waiting

Jessica, account exec, San Diego

My ex-boyfriend Blake and I started as friends; this was way back in college. We were friends through most of college and by our junior year we finally got together. He started sort-of-pursuing me earlier in college, but I wasn’t really that interested and it didn’t deter him from starting a friendship with me. He even wrote an article for the (UCLA) Daily Bruin about turning girl “friends” into girlfriends.

I was always attracted to his confidence in himself and his don’t-take-no-for-an-answer approach. Plus, it helped that he asked me to a weekend formal event through his fraternity around the time I was breaking up with someone else I wasn’t that interested in. Anyway, once things went to that “next level” from friends to dating, it just felt natural. I can’t say that most of my guy friends were people I would never have considered dating, though. With Blake it helped that he and I maintained contact throughout college as friends, and there was always a flirtatious element of our friendship.

From roommates to romance

Courtney, caterer, Ann Arbor, Mich.

I only know of one friend where it worked to make a friend “more.” Her name is Cara and she grew up together with her current boyfriend. Their families were best friends. Side note: he was my high school boyfriend! Anyway, they were roommates first (after college), and then they hooked up one time when they were drunk. THEN, they actually started dating. They have been dating for three years and he bought a house last year that they now live in together.

Flirty friends

Elizabeth, fashion director, New York

My boyfriend from high school, who I started dating our senior year, and I were friends since fourth grade. We always flirted and had our eyes on each other but never hooked up until, out of nowhere, we did one day. I think he was sick of my bad relationship stories and finally came to my rescue. We dated for two years and almost bought a condo together, but it didn’t pan out with a happily-ever-after story. I will say one thing, though, he always pops up in my dreams and I have this feeling it’s because we were friends for so long before we knew each other and I know for a fact he, of all the guys I’ve dated, had the most respect for me because he knew me the best. So I’m always going to be looking for that and I think it’s my inner psyche reminding me.

Childhood friends reconnecting on Facebook

Shane, web designer, New Brunswick, N.J.

I knew her since she was younger, about 13 at the time, and I was 17-18, so we were just like brother-sister. She used to come over all the time with her best friend whose mom was best friends with my mom. They would sleep over and always want to hang out with us, the older kids. She came over for about two to three years and then I went my way and hadn’t talked to her in forever.

We reconnected on Facebook years later when she was 23 and I was 27 and started hanging from time to time, but she was in a long-term relationship and I was in about 3,048,303,820 relationships. After she broke up with her boyfriend we started hanging out a little more, and we got a little flirty over time. It was always awkward trying to push the friendship into a relationship. So I think we both waited until a really drunk night and went at it. Now we’re in a serious relationship and moving in together. I slowly made it flirtier until I knew there was a chance and then it was kind of a mutual thing. We were both like (more her then me) “let’s get really drunk” which also meant “let’s hook up and let alcohol be the excuse for it” so that we don’t ruin a friendship.

Mutual interests in hobbies and each other

Amelia, writer, Los Angeles

I first met my current boyfriend many years ago, shortly after I moved to Chicago to do theater. I saw a play he wrote and acted in, and was so impressed that I went to talk to him afterwards. We flirted a bit. But we were both seeing other people, so nothing really happened. Over the next few years, I did two plays with his theater company, though not with him, and became friends with the same social circle. After I moved to LA, I saw him once or twice at parties, including the send-off when he got married. A couple of years later, I heard he was divorced. He moved back here and in with mutual friends. He friended me on Facebook, and I hooked him up with a teaching job. Last June, just as I was extricating myself from a particularly stressful relationship, he emailed me with an overdue thank you, and said we should hang out. I invited him to join me and a pal at a tribute to Fred Willard. We laughed until we cried, and afterwards hung out with other friends of mine. It was a great night. I was happy to reconnect and share my beloved LA with him.

We went out to a few more movies in the following weeks. Then one night he suggested we skip the movie and just go to a dinner party in Laurel Canyon. As we arrived, the host’s wife asked us if we were married. We laughed. Several drinks later, she sat down with us and advised him to kiss me. His eyes lit up. “You might want to listen to her,” I muttered. A short while later, he did just that. It was an “Aha!” moment for us both. We share many friends, both know theater, love good food and travel, and geek on an equally wide range of topics. When we discovered that we also enjoyed kissing each other, it felt like we had the whole package. And we’ve been having a delightful time ever since.

Friend zone is not the end zone

Mike, TV show host, San Francisco

She was not my type. And I wasn’t hers. We were largely invisible to each other. Then through a fluke in our college acting class, we were forced to work together. Both of us were not exactly thrilled about it, but we made the best of it. As we worked on this lengthy project together, we had a few laughs. We became friends. And we talked about the people we were seeing. It seemed we were both going on one bad date after another with people who were just wrong for us. Then one day, toward the end of our project, I saw her head down the hallway to another class. It occurred to me that unless I reached out, I might not see her. At that moment, I realized that I had more fun with Barbara than anyone I knew. I had to ask her out on a “date” date. We moved slowly, not wanting to ruin a real friendship. Then without even noticing how it happened, our relationship moved with the greatest ease from the friend zone to lasting love. We’ve been married for 25 years, and I know that I’m a lucky guy. The Friend Zone is the most natural place to find real love, if you listen to your heart.

These are just a few examples to learn from that offer proof and hope that it can work if you have the courage – liquid or otherwise – to make it work.

(Debra the Dating Diva is a Los Angeles-based dating coach and writer. When she’s not charming the men of Los Angeles, she’s cataloging her dating adventures and giving men the inside scoop on what women want them to know at her website blackbookbuilder.com. Got a dating question for Debra or her panel of ladies? Drop her a line at blackbookbuilder@gmail.com.)