Bringing a Friend on a First Date with Online Dating

Published on June 5, 2011

From time to time I see online dating safety advice offering this as a suggestion: bring a friend with you on a first date.

I understand the need to be safe but I really dislike this suggestion. Mostly because I had a woman bring a friend on a first date with me and it really hurt the odds of having another date (there wasn’t one). Admittedly, I found her approach as annoying as her actions…so I guess a full story is in order.

Photo by Desiree N Williams

I Hope You Don’t Mind but…

As I discuss in my online dating guide, there were several periods of my online dating life and this date came just as I was beginning to enjoy online dating. I was doing my very best to remain open about all dating opportunities but I was also becoming more assertive in not endlessly chasing one woman or anything else that I felt was wasting my time.

At any rate, I had been talking to this girl (who we’ll call “D”) for about two weeks and we had decided to meet at the Pittsburgh’s Carnegie Museum of Art. At this point, I thought everything was fine: she’d given no indication that she was nervous about meeting someone from the internet and as far as I knew she was looking forward to meeting as much as I was.

From Bad to Worse

I arrived at the museum a bit early to buy our tickets and around that time I received a phone call: she was about 10 minutes away and she was coming with a friend.

This surprised me and honestly I felt let down: things were suddenly feeling much less like a date. At this point I didn’t even have a guess as to why she would want to do this (as a guy safety isn’t something that is always going through your mind). Still, I was trying to change my approach and be more open so I decided to try to make the best of it so I bought a third ticket (make a good first impression with her friends, right?)

Photo by Desiree N Williams

When they arrived I suddenly realized meeting two women on a first date was even more awkward than I thought it would be. Little did I know that things would only continue down the path of awkwardness even further as the date moved forward. Specifically, there were large portions of the date where I didn’t even feel like I was on it: D and her friend were giggling at this or discussing that while I tried to work my way into the conversation.

Honestly at this point I’d say my interest level was just about dead. I was very disappointed because I had gone in with high hopes and I suddenly found myself going from excited to surprised to frustrated to feeling like I was just wasting my time. I guess some of this must have shown because near the end of museum it was obvious that D was trying to put an effort into actually going on a date with me.

Now She’s Interested

At the end of the night her friend drove herself home and I agreed to take D home. Here I finally had one-on-one time with my date and she even dropped hints that she was interested in seeing me again…but I had already decided to move on at this point.

In the past, when I was having trouble getting dates, I probably would have dealt with this and continued dating her. However, I felt like this wasn’t the last “game” we’d be playing and I had no interest in wasting my time when there were dating services full of women I could contact.

Honestly to this day I still have no idea why D thought bringing her friend would be a good idea. She never showed signs of nervousness or concerns for safety and I would say she was bubbly and out-going. Your guess is as good as mine.

If You’re Going to Bring a Friend on a First Date

If you’re thinking of bringing a friend on a first date…first, I recommend against it. There are other ways of making your first dates safe such as:

• drive separately
• meeting in the day at a public place
• schedule to only meet for 30 minutes
• let a friend know where you are and have them contact you at the time that your date should be over.

Photo by Allie_Caulfield

1. Make Your Intentions Clear Early

From the very start you need to be preparing the guy you’re meeting that you take extra care on first dates. Don’t call him on your way there and mention that you’re bringing a friend! Make sure he knows that you’re nervous about dating online or safety or whatever and let him know that you’d like to bring a friend on a first date. Just springing it on someone is likely to end up with them having the same reaction as me

2. Suggest a Double Date

It would be even better if you were to encourage him to bring a friend as well. This could change an awkward situation into a fun one where you and your date get to play matchmaker for yourself and possibly a friend as well. Had D suggested this I would have thought it was a creative and fun idea and would have been happy to bring a friend.

3. Don’t Forget Who You Are on the Date With

I think I might have been able to get past the fact that my date with D had 3 wheels…if I hadn’t of ended up being the third wheel. I actually thought to myself “I hope her friend doesn’t get bored while D and I talk” before they had arrived. Oh, I couldn’t have been more wrong on that one! Just keep in mind that you should be on a date, not hanging out with a girlfriend.

4. Plan with Your Friend for Her to Make an Early Exit

You may find yourself on a date where it turns out that the guy isn’t a psychotic killer who is executing an elaborate plan to get you down to down to the local Starbucks. If that’s the case (and it will almost always be the case) why not plan with your friend to have her leave early when everything looks fine?

Again, I think bringing a friend on a first date is overkill. To me, driving separately to meet at a public coffee shop at 5PM and leaving after 30 minutes is safe. If you’re really nervous, why not opt for that approach? If you can’t resist bringing a friend, at least consider my experience and consider taking some of the suggestions above.

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Author: Brad

Brad initially struggled with online dating but over time became quite successful using it. He met his wife using online dating and has been giving advice and helping people improve their results since 2007. He has written a Free Online Dating Guide to help others find success with online dating. You can learn more about his personal experience using online dating and running this website here.

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