15 Funny Things First Dates Turn Into (Like Therapy Sessions)

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Reconcile With His Ex

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People go on first dates for all sorts of reasons. Sometimes those reasons have nothing to do with trying to find love or even a romantic fling. Admit it: you’ve opened four online dating accounts in a moment of insecurity/brokenness /horiness/loneliness/confusion/anger/curiosity and so much more.

So, it should come as no surprise that the people you meet online may be doing the same thing. It should also come as no surprise that many first dates don’t end in any normal way, like a plan for a second date, a mild makeout session, or even a one night stand. Nope. Some dates end in very, very odd ways. Sometimes we can help our dates in ways we never knew. Sometimes our dates can help us in ways we never knew! And none of them have to do with putting a ring on it, or a Facebook relationship status on it. Here are bizarre things first dates can turn into.

An alcoholic realization

I had one first date get too drunk, try to grope me a little too much, and fall asleep in our booth. The next day he called, and he said, “Our date made me realize I can’t handle social situations without alcohol. I’m going to quit dating for a while to go to AA and figure this out.”

The “How do I get my ex back?”

Then there are the guys who, while in the process of telling you about their last relationship, realize that they want their ex back. Then they have the gall to ask you for your advice on how to make that happen.






The jealousy ploy

One friend had a first date take her to a restaurant where his ex-girlfriend worked. He sat with his arm around my friend the whole night, staring, vindictively, at his ex.

The life path realization

I went on one first date with a guy, where the date ended up more like a career counseling session. What started as an innocent, “So. What are your aspirations?” question from me, ended in an hour and a half long vent session from him about how confused he was about his path.

Image Source: Shutterstock

Image Source: Shutterstock

The proposal

I haven’t had men propose to me on first dates, per say. But I have had them give me their assessment of whether or not I would make a good wife for them, along with the question, “Would you be willing to get married in the next half year or so?”

The gay guy turned…gay

My friend went on a date with a guy who confessed he’d only dated men his whole life—he was just seeing if women were for him. They still weren’t.



The, “Look, mom, I’m on a date.”

I went out with a guy who called his mom in the middle of the date to tell her he was on a date so she could, “Stop worrying already! Okay! Here. I’ll put the girl on the phone.”

The therapy session

I’ve had a lot of first dates turn into therapy sessions. Plenty of men are just looking for a relationship to distract them from their personal issues. I made the mistake of asking, “So. Would you call yourself a happy person?” and boy did I get an earful.

Black couple money/finance/budget


A finance counseling session

One poor guy had his credit card declined on our date. When it happened, he said, “This happens all of the time. I’m not very good with money.” We ended up discussing his financial habits, and ways he can put aside more money.

The booty call precursor

One unfortunate friend went on a date with a guy who had her drop him off at another woman’s house afterward.







Helping with his dating profile

One guy and I were so obviously incompatible. The guy said to me, “I keep getting matched up with girls who are obviously wrong for me.” So, right then and there, we went over his dating profile and edited it to better depict who he really was.

The fanboy

I have one friend who does standup comedy. She went on a date with a guy who professed to having found one of her standup sets online a long time ago. He followed her on Twitter, figured out what dating apps she made jokes about using, and BAM found her on one. EEEEK!







The networking date

We’ve all had it happen: we go on a date with somebody who we realize we could never romantically be with, but who we could network with. You’re in the same industry, you know the same people, you could really help each other out.



The makeover

I went out with one guy who insisted and insisted I tell him if he “Had it going on.” He wanted to know if his hair was attractive if his facial hair flattered him and if he dressed in a way women would find attractive. We ended up going shopping.

Divorce - Sad young couple holding billboard sign with break up



I went on one first date when I was just trying to get over an ex; it turned out my date was trying to do the same thing. We drank a bunch of wine and commiserated like a couple of best friends.

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