How do I approach maintaining a friendship with someone I used to date, who now has a significant other?

Question

Background:

I'm a single 20-something man living in a major city who is actively dating. I met a woman about 5-6 months ago on a dating website, let's call her Alice. Alice and I hit things off well based on our mutual interest in early modern music and modern Japanese authors. We went on two dates to shows and had a great time each evening. However, soon we mutually decided we didn't want to pursue a relationship, but wanted to still be friends and continue to go to music shows and talks about books together. So we did; maybe seeing each other about once a month, and texting a handful of times a week to work to pick out shows, work out logistics, and occasionally share work/life updates in a way that's typical of friends.

Problem:

Just recently Alice got a boyfriend, call him John. Last time I saw her, she expressed concern to me that she might no longer be able to be my friend because of the circumstances in which we met and what that would cause John to think. Nevertheless, she was willing to keep contact as a friend for now. Normally when I'm in this situation I'll try to arrange a double date or something similar so I can meet John and demonstrate I'm not a threat to him, and just generally bring things into the open. However Alice seemed less than thrilled at that idea. This made me a little uncomfortable that our friendship might be somehow secret, and poking at this further she explained it's just embarrassing to tell people, not exclusively, but especially her boyfriend, how we met despite the fact that we are just friends now.

Question:

What is an appropriate way to approach a conversation with Alice to ask her why she is bothered by telling people we met online? How can I ask her how we could make her feel more comfortable with introducing me to her social circle?

I would like advice on how to approach a conversation about how we can be friendly enough that we could introduce each other to our wider social circles without how we met getting in the way.

Answer 1

Approaching Alice

texting a handful of times a week to work to pick out shows, work out logistics, and occasionally share work/life updates in a way that's typical of friends.

Begin the conversation over one of your normal communication mediums, in your case via text. I favor this as it feels more natural, and will probably be more comfortable for Alice than calling out of the blue.

Keep your texts shorter. You have a lot to say, but responding to lengthy message can feel especially daunting to someone who is already feeling uncomfortable.

Reread your texts before sending. Ask yourself: "Have I repeated myself?" "Can I say this at another time?" "Is saying this essential to this conversation?" You may also decide that you would rather have a conversation in person, in which case you can make plans to meet.

Lastly, you should utilize a classic interpersonal skill and use "I" statement instead of "You" statements. Remember that this is centered on how she feel about you and her relationship with you, and she won't feel comfortable discussing this or potential solutions if she feels overwhelmed, threatened, or as though she is doing something wrong.

"I feel A when B" instead of "You C and it makes me D"

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Offering a Solution

Remain calm and thoughtful of her position. She is in a delicate place with her new SO, and as a new friend yourself, you need to respect this.

she expressed concern to me that she might no longer be able to be my friend because of the circumstances in which we met and what that would cause John to think

It sounds like the main issue here is is how people will perceive the fact that you met on a dating website. I see that your solution is to simply keep that chapter of your lives private, or to be entirely forthcoming.

As she feels uncomfortable with the latter, your only option left is the former. Ask Alice if she is comfortable with keeping this to yourselves. You are both adults and can discuss how much you feel comfortable sharing with others in your lives about the nature of your relationship's foundation. It is perfectly okay to tell your friends "We met at [your first IRL meeting], and have been friends ever since!"

The friendships and relationships being discussed are relatively young -- the dating website bit can be disclosed at a later date, when foundations have been established and all parties involved are comfortable with their standing.

This made me a little uncomfortable that our friendship might be somehow secret

Right now, that is exactly what it is. If you are not okay with this, and she is unwilling to compromise, you should not remain in a relationship that will only serve to make you feel belittled or unimportant.

On the flipside, you need to be prepared to accept that she may want to cut off contact. This is incredibly painful, but please realize that this is not the end of the world. It is very common for relationships to ebb and flow with the introduction of new significant others, but friendships prove to last the long haul after romantic flames have fizzled into the past.

Answer 2

The answer is going to vary based on your social circle's norms and practices. In some of my social circles there are many cross-gender friendships and it is extremely common for people to date or even marry, break up, and continue to happily be part of the same circle or even specifically direct friends. In others, a friendship with an ex is automatically suspect.

I have dated people who felt uncomfortable with my friendships with exes. It's... awkward. Mismatched expectations are rarely easy to align.

In your case it may be easier because you don't have an extensive dating history with Alice -- it sounds like you went on a couple of dates but there was no spark.

But if John can't accept Alice being friends with a previous partner, no matter how limited the partnership, that's something Alice and John are going to need to work out for themselves. (It's also possible that John is uncomfortable with all of Alice's male friends.)

(This is rather similar to my current situation -- while I'm on friendly terms with most of my exes, because I've moved away from most of them the only one I see regularly is D. And in fact D. and I met on a dating website, and he introduced me to a hobby we now share. Some people might think it odd that I travel to a hobby event with someone I used to date for a few months... but if I liked him enough to date him, why wouldn't he be a suitable friend?)

So, specific advice. If I were you, I'd approach it from a different direction:

Alice, it's a shame that we can't do things together since you started dating John. Is he bothered by all of your male friends, or just me because we went on a few dates? Or is it that you're embarrassed to admit that you used a dating website?

Is there something I can do to make this situation less uncomfortable for both you and him?