How To Try To Reconnect With The One That Got Away

How To Try To Reconnect With The One That Got Away

This week we have a man that met the girl of his dreams, but work got in the way before romance could blossom. Is there a good way to contact the one that got away and rekindle the magic?

Some people have problems that require delicate advice from a qualified professional. Others just need a random guy on the internet to kick ’em in the teeth (with honesty, that is). I’m the latter. Welcome back to Tough Love.

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Note: I’m not a therapist or health professional of any kind. People ask for my advice and I give it to them. End of transaction. If you have a problem with it, feel free to file a formal complaint here. Now that that’s out of the way, let’s get on with it.

Hey Patrick,

What is the best way to get back in contact with a former interest that faded out? I met this woman at a bar a few months back on a Saturday night. We spoke for a few minutes, made each other laugh, exchanged numbers. The problem is I have an extremely busy job that is about 90 per cent travel, so dating has been close to impossible these past two years.

When I texted this woman for the first time she seemed pretty enthusiastic about meeting. We set up plans to go get drinks the upcoming Thursday, but another unfortunate thing about my job is the travel is totally unpredictable. I got a call from my boss on Wednesday morning telling me that I had to fly out to Atlanta that night, so I had to cancel the date.

We rescheduled, then I got called out again. And again. And again… It was three weeks before this woman and I could finally go on a date. Usually when this happens, women lose interest before we hang out. The fact that she still wanted to hang out after I cancelled so many times was astounding to me.

The date was awesome! We had a lot in common, had the same sense of humour, and a lot of chemistry. Unfortunately we were never able to hang out again. My job sent me out again and I was gone for 10 straight weeks. We kept up through text and calling at first, but over time it just faded out.

I’m starting a new, more stable job at the end of the month and I’d like to try again with her. But I honestly don’t know how to rekindle something that’s been dead for two months. What should I say? Is it possible? Would I be a jerk? Should I just move on and try with someone else?


Weary Traveller

Hey Weary Traveller,

The good news is it sounds like she was into you, things didn’t end badly between you two, and it hasn’t been a super long time since you last talked – so there’s still hope. The bad news is that she may have already moved on by now. Two months of radio silence doesn’t mean she’s already betrothed, but that’s plenty of time for her to fall head over heels for someone else and forget about you.

Whether she’s found someone else or not, you’re in a good position to contact her – assuming your availability is actually improving. If you can guarantee you won’t be such a slippery devil now, she might be just as interested in starting things up again. The key here is to tell her about this impending change to your life, and how it will be easier for you to get to see each other and get to know one another. So, Traveller, send her a text message like:

“Hey, it’s [your name]. I hope you’re doing well! I’ve been crazy busy with work for the past few months, but I’m switching jobs soon and won’t have to travel as much. I know getting together was difficult before, but I’ll be a lot more available now, and I’d love to reconnect if you’re up for it!”

If you had an inside joke together or special memory of some kind, it doesn’t hurt to mention that either. Remind her that you guys had fun, and that you haven’t forgotten about the time you had together. Then, add this to your message:

“If not, no hard feelings, and I wish you the best!”

It’s totally fair for you to reach out to her – it doesn’t make you a jerk – but it’s also only fair for you to give her a way out. Also, manage your expectations before you hit that send button, Traveller. You might only get a quick “No thanks!” or you might get no response at all, which is totally justified at this point. She doesn’t owe you anything here, so keep that in mind.

That’s it for this week. I probably didn’t make you feel all warm and fuzzy inside, but sometimes what you need is some tough love. ‘Til next time, figure things out for yourself.

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