Ask Erin: Should We Stay Friends Or Give This Relationship A Chance? 

When friendship becomes something more...

When friendship becomes something more...

She’s made all the mistakes, so you don’t have to…Ask Erin is a weekly advice column, in which Erin answers your burning questions about anything at all.


Hi Erin, 

My friendship of 30 years has turned into dating. We've known each other since we were teenagers. He dated a few of my friends and even had a baby with one of my friends (25 years ago). 

He has never been married, but was engaged once. We lost contact when I got married and moved to New Jersey, as he lives in Florida. 

A couple years ago, we reconnected on Facebook as friends. Last October 2015, I went to Jacksonville to visit him for a few days. We ended up being intimate and having sex. Fast-forward to August 2016 — I saw him for a couple of days again which turned into six weeks in Jacksonville. 

I am back in Tampa with my family and he says he would still like to try this relationship. Things were great at first. He was texting me, telling me I'm beautiful. And then a few weeks ago, the texting was still there every day (couple times a day), but not as sexual or flirtatious as before. 

Now for the downside — I have been legally separated for a few years and am going through the divorce now. He's a little nervous about that and kind of stepped back, but we are still going to date. He says that once I am divorced he wants me to come stay with him.  

My question is: should we go ahead and pursue this and see where it takes us? We have been the best of friends, and we are both very happy that we were able to reunite again with each other after 25 years — but should we stay friends or go ahead and give this a shot?

I adore him and he adores me, we love each other to the extent that the sex is great and we have fun together. It's just that now that I've left Jacksonville and am back in Tampa, the text messages aren't like they were before. 

We do talk daily, sometimes a couple of times every day, and I do have plans to go back there in a couple weeks to see him (before I head up to New Jersey for the holidays to be with my children and then I'll be back). I really don't know what advice I'm looking for, other than am I doing the right thing, are we doing the right thing, by giving us a go?


So you’ve found love again in an old friend. You wouldn’t be the first, and I’m sure there’s been a whole lot more of this since the advent of Facebook. 

The great thing about a romance with someone you have known so long (albeit with a large — read: 25 year — gap) is that they understand a significant part of who you are and where you came from, the places and people who shaped you in those formative teenage and early adult years. 

It sounds like what you’ve got going with him so far is pretty great. As you said, you adore each other, the sex is great, and you have fun together.

These are HUGE factors in making a relationship work. But, is it enough? 

Let’s look at the downside, as you called it — you are in the middle of a divorce. Even though you are separated, it’s not a done deal, yet. I can understand his trepidation. Unraveling a 25-year marriage (I am assuming here based on your timeline) can be thorny: not because you might get back with the ex, but because letting go of that history with someone, even when it’s all done, is a process. 

Despite that, I think there’s no reason you shouldn’t give this a go. Will this be the man you spend the next chapter of your life with? I don’t know. But, instead of hedging your bets (the same could be said for him, too), enjoy the time you have — enjoy the sex, the adoration, and the FUN. 

The worst thing that can happen is that it doesn’t work out. That won’t make the time you spend together, in the present, any less valuable. 

Lastly, a caveat about worrying too much about the nuances and frequency of his texts. While being ignored/iced out is one thing, I think it’s normal and natural for the communication in a long-distance relationship (and even in an in-person relationship) to ebb and flow. Dynamics are fluid and we all have so much going on in our lives outside of our intimate relationships. 

Take a breath, live in the moment, and see where this takes you. 

If you have a question for me about love, sex, relationships, breakups, what I’m reading, self care, Bismuth, or anything at all, use the contact form below or email me at As always, your anonymity is golden. xoxo

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