Online dating question

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Episode 36: You Tube sensation, a father’s appreciation, pajamas in public

Hi guys,

I recently came across your Podcasts and I wanted to let you know that I really enjoy and appreciate what it is that you guys do. It’s refreshing to hear from men that can seriously answer questions from women without a bunch of high-fiving and smart comments!

So here’s my question… About 3 years ago I was in a relationship with a man who died unexpectedly. We hadn’t been dating that long but I was still pretty shaken up by the experience and have been a little gun-shy about dating since then. A friend of mine suggested that I give on-line dating a try so I did. After having a profile up for a few weeks I started corresponding with a man which eventually moved into talking on the phone. He lived one town over so we decided to get to know each other a bit before committing to a visit. I felt like we were really hitting it off… we would talk sometimes for 3-4 hours at a time, always laughing and having conversations that I really enjoyed. We talked on the phone every night for about 10 days in a row when we started to make plans to meet. I was really excited about the possibilities and just knew in my heart that I would get along really well with this guy. Then, one night during our conversation he asked me why I wasn’t currently in a relationship so I told him about what had happened with my last boyfriend. He was very nice, acted like it was no big deal and even offered to listen if I ever wanted to talk about it. So we said goodnight soon after and I went to bed. After that I never talked to him again… I received a few text messages but eventually those died off as well. Needless to say, I was disappointed but I tried to take it in stride. I realize that not every person that I meet or talk to is going to be interested in me.

My question for you guys though… do you think that revealing to this guy that my last boyfriend had passed away could have scared him off? Should I not tell people that I meet in the future about it? I try not to make it a big deal but it does affect how I think about relationships, so I want to be upfront, but I don’t want men thinking that I have a ton of emotional baggage either. Also, I know that you can’t read his mind but could you try to give me some kind of insight into what he could have been thinking? I’m trying to be practical about this but it still hurts when you think that you’ve connected with someone and they disappear.

Thanks again for all that you do!


Dear Megan,

Thanks for your question.

We’re sorry to hear about your ex-boyfriend. Whether you knew him a month or ten years, it’s never easy to have someone die, especially unexpectedly. But you still sound open to beginning a new relationship, even as you deal with the loss. So that’s a positive moving forward.

We think it might have been too soon to tell this man about your past. Not all men are going to be spooked, but he definitely was. We’re curious how you told the story, or how you plan to tell it in the future? Your instincts are good about being open, and not hiding your past, but there’s a time and a place for everything. And there’s also a HOW. Since we don’t know the details on what happened with your ex, we can’t say what the best way to approach it is, but we will say there’s definitely many ways to tell your story, and you have to think carefully about the best way to open up. And of course you’ll have to modify it for each person, since everyone is different.

Now as far as WHEN to say something: If someone asks you again why you are single, just tell them you’ve been in a few relationships that didn’t work out and leave it at that. You’re not lying, you’re just holding off on a few details until things are a little more solidified with the new person. And by that we mean going out on actual dates over a few months or so.

Unfortunately you’ve acquired baggage from your past. Like people who are divorced, or those with kids, you now come with a more complex bag of “stuff” than the average single person. Of course you don’t mention how old you are, so we assume you are younger than most “widows,” which might be the reason this guy got spooked.  Guys don’t expect to hear about ex-boyfriends dying if they meet a girl in her twenties, thirties, and maybe even forties. And it’s definitely enough to cause him to bolt because he assumes you’ll be coming with a lot of emotional baggage, as you feared. But once again, only because it was too soon to tell him, and because he didn’t know you beyond your conversations on the phone. He pictured you as this fun loving, smart, sexy woman, and after you told him about your past, that perception changed. The fun loving piece was likely replaced by a much more serious image of you, which he wasn’t ready to deal with. We’re sorry. It isn’t fair, and isn’t cool, but at least you’ll know moving forward that you have to be a bit more protective of your past, at least at the beginning.

And finally just to reiterate, think about how you want to deliver this message to someone new. Ultimately the right person will accept you for who you are, and what you bring to the table.

Good luck,


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3 Comments on Online dating question

  1. Yet again I agree with the Guys. There is a time and a place, and it seems like it was just too soon to share that info.

    Also, I’m very sorry for your loss.

  2. Thank you for answering my question… but I have to say I was a little upset by your answer. I guess that it just wasn’t what I was hoping to hear. It upsets me that some men are shallow in even more ways than I already knew but I will definitely follow your advice in the future.

  3. @Megan…..We’re sorry again Megan, for your loss, and for your current situation with this guy. Not all men are like that, but we were trying to explain why this particular guy might have had second thoughts.
    It’s not necessarily about being shallow, although this guy seems kind of lame to not at least give it a go with you since you were connecting so well on the phone. Some guys—or really some people—want to start their relationships as lightly as possible, since ultimately relationships are very complex and sometimes hard. That’s not to say they’re not worth it. They definitely are. But the better a person gets to know you over time, the more they will be open to every part of you: past, present, and future.
    Hang in there. And good luck. We’re sure you will meet someone who loves you for you. Take care.

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