Question: Should I be concerned about an attractive, funny guy who casually mentions that he had a fiance in college during our first phone conversation?

Now, it’s important to note that he went to a school in Nebraska and says it was “young puppy love.” I’m thinking it’s probably OK. And so, the conversation continued.

We’re on the phone for quite a while. He is funny, he had lots of questions to keep the conversation going he had sent some fairly hilarious text messages earlier in the day. I’m thinking I can look past the college fiance…not a true red flag.

So, later in the conversation, he casually drops that he was engaged. I’m thinking, ”yeah, we covered that.”

But, as it turns out, he was, in fact, engaged twice…once again in his early twenties. (The red flag creeps back up).

This is a tough one. If the roles were reversed, I could certainly picture a girl saying yes to a proposal in the heat of the moment and then eventually backing out if she wasn’t sure. Maybe she was taken off guard and all eyes were on her when he pulled out the ring…what have you.

But for a boy, there’s the planning, the buying of a ring and the very strong desire to be with that girl forever. And this cute, funny boy has been through that twice and he’s mentioning it to me on our first phone call.

Now this could be taken a number of ways:

On one hand: He’s a guy that is open about his past and likes to commit.

On the other hand: He’s a guy that probably has an issue with follow-through.

One hand: He’s never been married, or divorced and doesn’t have any kids.

Other hand: If it works out, there’s high probability of a hand-me-down ring in my future.

I think I’ve proven to be fairly open-minded in my dating habits, and there was a lot of “good” on the phone call tonight, so I’m going to give this further investigation.

That said, my “alert-antenna” went up when we were texting again after the phone call and he responded to one of my (witty) texts with this joke:

“Oooh I like that! We are going to get married for sure.”

Footnote:

I looked up the origin of the saying “third times a charm” and found this on WikiAnswers:

The first citation I can find for it is in The Weekly Sentinel, June 1912. This is in a rather snooty court report about a Mrs. Martha Carliss, who had been twice married previously:

That Mrs. Martha Carliss evidently believes in peace and happiness in wedlock and that she probably thinks third time’s a charm is shown by the fact that she was granted a license today to marry Andrew W. Mowery.

You decide:

I recently went out with a guy and while date #1 had it’s fair share of red flags, it took date #2 to show me the light.

First Date Red Flags:
#1: He chose a dinner location around the corner from his house and a good 10 miles from mine.

#2: The inner thigh of my jeans ripped while exiting my car at the restaurant valet – I believe the universe was raising a red flag for me. (Side note: A woman walked in on me while I was taking this picture – leg up on the sink – in the restaurant bathroom. It only showcases 1/2 of the rip).

#3: During dinner, he reached across the table, pointed to and physically touched a zit I had covered up on my forehead and asked if it was a scar. I mean…not only did he notice it, he made mention of it and forced me to admit to my B-looking girl, adult acne on a first date.

#4: He surprise kissed me 3 times, to which I would unconsciously and uncomfortably react with an “oh dear” just before he kissed me.

#5: At 11 PM on this Monday night date, he asked me if I wanted come over to his house and to watch this random independent film where the leading lady shares my first name.

After all of that, I still accepted date #2 to go see that independent film at a once-a-month-showing in a theater. I figured it would be a cultural experience and could avoid any more invitations to go to his house to watch it.

Little did I know that it would be a midnight showing of “one of the worst films ever made” (according to Wikipedia) at a theater 20 miles away from my house. Not only did this film have a following of obnoxious people who waited in line for 2 hours to get a good seat and insisted on yelling throughout the screening, it was essentially a soft-core porn, cast with unattractive people. I wanted to leave the instant it started. How could he fail to mention the numerous poorly-shot naked sex scenes when “selling me” on the date?

In hindsight, I should have simply left, but at the time I felt trapped and so…since it was 1 AM and I was in a dark room looking for an escape from the experience, I allowed myself to fall asleep. Still think it was wrong?

You do? Well, what if I told you that he has seen the movie over 15 times, owns the DVD, has been to the midnight screening two other times and has a picture of himself with the director on his cell phone?

…I thought so.