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So you got a date with that cutie

The connection

So, it was a couple years ago. I had recently become “friends” with a little hottie on Facebook at that time. My life was in a bit of “disarray” so to speak, but nonetheless I still wanted to prospect for cute girls on Facebook, I mean who doesn’t when they’re single? So for the first couple months if I do recall correctly, she just shared, or made comments about things she liked or would get people talking and I would chime in here and there. Eventually, we found or liked an event we were both interested in. We chatted in messenger about it, and we set a date. She picked me up and we went into the big city. It was a day-time date, and I believe, I had just finished plowing snow the day before.
    So we go to the event, gallery, show- whatever specifically it was. We walk around, have a good time. We go down to a local eatery in Portland, ME; we’ll call Pablo’s, delicious I may add; had a couple of drinks and a late lunch. She had something to do by mid afternoon. I met back up with an associate of mine in town, and went about my business.

Our continued friendship

Now, I’m pretty sure we both had a good time, but life as you may have it went on it’s course and we didn’t connect in person for a few months. Sure, there was the back and forth- comments and likes on Facebook, and the few messages back and forth. But, when something just isn’t working, you can’t push it and force it. It’ll only push away harder, like magnets with reverse polarity. Anyways, fast forward again a few more months to my summer birthday.Somehow we connect, again..


Starts as a day date we go to lunch at some place on the coast of Maine in Kennebunk, York, Wells, that area. Have a few drinks, go for a walk along Maine’s beautiful rocky coast. Her sandal breaks, lol. I needed new ones anyways, so we go to Reny’s for new shoes. Now we’re having a pretty good time, tbh and it’s only mid afternoon. So, I call up my friend and his fiancee to see if they’d like to join us for dinner, they agree. We pick them up and head to a place in down-town Portland, ME– the Old Port district, on the waterfront. She falls asleep on the way there. I have dinner with friends, we start heading home to drop them off. She wakes up, hungry of course. Lol. We go to a place closer to where I live in Gorham, get something to eat and head back to my place. I ask her if she’d like to spend the night (in the same bed- more on that later), and have me bring her home in the morning. She agrees.

I bring her home the next morning, say goodbye and go about my way. Again, same situation. For some reason, we don’t connect again, and several more months go by. Trust me, it’s not for lack of trying. I mean, she’s cute and fun. but it’s just not working out for meeting up in person again. So fast-forward to the fall, and I post something about looking to get something to eat at Pablo’s, as it’s one of my new favorites. Of course, she responds to it and we start messaging.

The Result

We meet up at the restaurant, talk, she informs she has moved into a new place in town. We eat, drink, and are just having a really good time. We decide to move along to another place in the Old Port and run into a friend of mine and his lady friend. We end up hanging out most the night until almost midnight before we decide to go. We part ways with friends and end up back at her new place. Another good night down, the next morning/day not so much. Little sleep, coupled a slight hangover and having to help her move in a few things, along with having to retrieve my roommates vehicle from the airport didn’t make for the most stress-free day.

The Lessons

So after parting ways that following afternoon, as you can expect, things went as they did prior. She has a boyfriend now. We are still friends. We still talk. We still interact on social media. There are a few reasons for sharing this story. First one is, very few people will know who she is because neither of us plastered or posted on social media or tagged each other when we went on a date or hung out, which is part of the reason I’m willing to share. It doesn’t make the memories any less real because we didn’t publicize them. The second reason is to point out to fellow guys to not pursue, or push a girl into something that isn’t just naturally happening because you won’t be friends, and you won’t have a chance to “sleep” with her maybe at all or again.

My 3rd is to the ladies, and that is even if your intentions were to just “make a friend” or even if you considered something more long term with a guy, don’t limit your intention. Don’t make a set of rules, so to speak. Now I’m not saying go have sex with every guy you “friend-zoned” (which I don’t believe in, but that’s another story), I’m just saying for the right people it’s possible to have sex and still maintain a friendship afterwards. (A committed relationship is a bit trickier). Now I don’t want to sound shallow, but I’m not sure we’d have the great, trusting committed friendship we have today if we didn’t. There is a certain additional level of trust you extend to someone by opening that door, and it can backfire, so trust your judgement, not your rules. Not all of us guys are obsessive psychos or players just looking to rack up the notches.

I’d like to add, although I am not as familiar with this- I probably wouldn’t apply this to that guy or lady friend that is like your real life top 5-7 people you hang out with on the reg. Chances are they have some real feelings for you already, and if you don’t feel the same for them, this could complicate that. (This may be a better topic addressed by someone else)

None of these dates happened by pressure. For those judging the “date count timeline” because it certainly wasn’t quick from first date to sex, just keep in mind, people like sex. I definitely would not consider 2 attractive adults (I like to think), who are not having not having sex with anyone at the time, would be more inclined to do so than those that are already.

I hope this inspires you to provide any positive advice for the dating and relationship community and perhaps you could share a story that could help provide positive insight to the dating community.

  • Anonymous

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